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inquiryWhy is SINOWAY: 1) Specialized in pharmaceutical and healthcare industrial for 34 years. 2) ISO 9001:2015 & SGS audited supplier . 3) Accept various payment terms : T.T 30-60 days. 4) We have warehouse in USA with quickly shipment . 5) We c
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inquirySpecification Product Name:5-bromo-2-chloro-4 '-ethoxy diphenylmethane Product number:BJM-035 CAS:461432-23-5 Molecular formula: 461432-23-5 Molecular weight:325.63 Content:99.0%min English name: 5-bromo-2-chloro-4 '-ethoxy diphenylme
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inquiryThe company serves as a key global supplier of statins intermediates, which has a solid industrial foundation in the field of statins for lipid-lowering drugs, and holds a leading position in the market. Leveraging extensive experience in research an
Cas:461432-23-5
Min.Order:25 Kilogram
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Type:Trading Company
inquiryDayangChem exported this product to many countries and regions at best price. If you are looking for the material's manufacturer or supplier in China, DayangChem is your best choice. Pls contact with us freely for getting detailed product spe
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inquiryItems Standard Result Assay (Ursolic acid) 98%min 98.22% ----------------------------------------------------------------
Cas:461432-23-5
Min.Order:1 Gram
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Type:Trading Company
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Min.Order:1 Gram
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inquiryUnique advantages of 5-bromo-2-chloro-4-ethoxydiphenylmethane Cas 461432-23-5 Guaranteed purity High quality & competitive price Quality control Fast feedback Prompt shipment Appearance:Almost white powder Storage:Cool dry place
Cas:461432-23-5
Min.Order:1 Kilogram
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Type:Trading Company
inquiryhigh quality Appearance:white powder Storage:Sealed, dry, microtherm , avoid light and smell Package:According to the demand of customer Application:Pharmaceutical intermediates Transportation:by air or by sea Port:shanghai
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Min.Order:1 Kilogram
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inquiryThe above product is Ality Chemical's strong item with best price, good quality and fast supply. Ality Chemical has been focusing on the research and production of this field for over 14 years. At the same time, we are always committed to providi
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inquiry1. Factory price and high quality must be guaranteed, base on 8 years of production and R&D experience2. Free samples will be provided,ensure specifications and quality are right for customer3. Customers will receive the most professional technical s
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inquiryCangzhou Enke Pharma Tech Co.,ltd. is located in Cangzhou City, Hebei province ,where is a famous petroleum chemical industry city in China. Enke Pharma a high-tech enterprise ,and we are dedicated to developing and manufacturing new ap
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inquiryProduct Description Product website: http://www.finerchem.com/pro01en/id/1059.html Product Name 4-(5-Bromo-2-chlorobenzyl)phenyl ethyl ether CAS No.
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inquiry5-bromo-2-chloro-4’-ethoxydiphenylmethane Basic information Product Name: 5-bromo-2-chloro-4’-ethoxydiphenylmethane Synonyms: 5-bromo-2-chloro-4’-ethoxydiphenylmethane;
Cas:461432-23-5
Min.Order:1 Kilogram
Negotiable
Type:Lab/Research institutions
inquiryOur advantages: 1, High quality with competitive price: 1) Standard:BP/USP/EP/Enterprise standard 2) All Purity≥99% 3) We are manufacturer and can provide high quality products with factory price. 2, Fast and safe delivery 1) Parcel can be
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inquiryhebei yanxi chemical co., LTD who registered capital of 10 million yuan, nearly to $2 million, we have a pharmaceutical raw materials factory production of pharmaceutical raw materials, and a reagent r&d center, and we do research and developmen
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inquiryName 5-bromo-2-chloro-4’-ethoxydiphenylmethane/4-(5-Bromo-2-chlorobenzyl)phenyl ethyl ether Synonyms 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene; 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene
Cas:461432-23-5
Min.Order:5 Metric Ton
FOB Price: $1.0 / 2.0
Type:Other
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Min.Order:1 Kilogram
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Type:Other
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Min.Order:1 Kilogram
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Type:Other
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Min.Order:1 Kilogram
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inquiryHangzhou Huarong Pharm Co., Ltd. established since 2009 , has been always focusing on supplying products and services to our clients in the field of small molecule drug. Huarong Pharm has built platforms for the research, development and manufac
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Min.Order:1 Gram
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Type:Lab/Research institutions
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Min.Order:1 Kilogram
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Type:Trading Company
inquiry5-bromo-2-chloro-4’-ethoxydiphenylmethane CAS:461432-23-5 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing
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Min.Order:1 Gram
Negotiable
Type:Lab/Research institutions
inquiryHebei Mojin Biotechnology Co., Ltd, Our company is a professional in lead acetate, diphenyl ethylamine and other chemical raw materials and chemical reagents research and development production enterprises. Our business covers more than 30 countries,
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Min.Order:1 Kilogram
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Type:Trading Company
inquiry(5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
With triethylsilane; boron trifluoride diethyl etherate In 1,2-dichloro-ethane; acetonitrile at 0 - 50℃; for 3h; | 97% |
Stage #1: (5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone With sodium tetrahydroborate In dichloromethane; acetonitrile at 30 - 40℃; for 0.5h; Stage #2: With chloro-trimethyl-silane In dichloromethane; acetonitrile at 30 - 40℃; for 3h; Stage #3: With boron trifluoride diethyl etherate In dichloromethane; acetonitrile at 0 - 35℃; for 8h; Inert atmosphere; | 96% |
Stage #1: (5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone With sodium tetrahydroborate In tetrahydrofuran at 10 - 15℃; for 0.5h; Inert atmosphere; Industry scale; Stage #2: With aluminum (III) chloride In tetrahydrofuran at -5 - 70℃; for 20h; Inert atmosphere; Stage #3: With water at 0 - 40℃; Inert atmosphere; | 94% |
4-(5-bromo-2-chlorobenzyl)phenol
ethyl iodide
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In acetone at 20℃; | 96% |
Phenetole
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
With aluminum (III) chloride In ethyl acetate at 78℃; for 9h; Cooling with ice; Large scale; | 89% |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
Stage #1: 5-bromo-2-amino-4'-ethoxydiphenylmethane With hydrogenchloride; sodium nitrite In water at -5 - 0℃; for 3h; Large scale; Stage #2: With hydrogenchloride; copper(l) chloride In water at 20 - 80℃; for 4h; Large scale; | 83% |
Stage #1: 5-bromo-2-amino-4'-ethoxydiphenylmethane With hydrogenchloride; sodium nitrite In water at -5℃; for 3h; Industrial scale; Stage #2: With copper(l) chloride In water at 20 - 80℃; for 4h; Industrial scale; | 83% |
Stage #1: 5-bromo-2-amino-4'-ethoxydiphenylmethane With hydrogenchloride; sodium nitrite In water at -5 - 0℃; for 3h; Large scale; Stage #2: With hydrogenchloride; copper(l) chloride In water at 20 - 80℃; for 3h; Large scale; | 79% |
Phenetole
5-Bromo-2-chlorobenzyl bromide
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
With zinc(II) chloride at 75℃; for 6h; | 71% |
(5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone
1,2-dichloro-ethane
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
With potassium hydroxide; BF3.Et2O; Et3SiH In water; acetonitrile |
5-bromo-2-chlorobenzoic acid
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 h / 20 °C 1.2: 3 h / 0 - 24 °C 2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 1 h / 0 - 24 °C View Scheme | |
Multi-step reaction with 3 steps 1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 20 °C 2: aluminum (III) chloride / dichloromethane / 1 h / -5 - 0 °C 3: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / -20 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 2 h / Reflux 2: aluminum (III) chloride / dichloromethane / 1 h / Ca. -12 - Ca.-8 °C / Inert atmosphere 3: triethylsilane / dichloromethane / 0.3 h / 0 - 15 °C View Scheme |
Phenetole
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 h / 20 °C 1.2: 3 h / 0 - 24 °C 2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 1 h / 0 - 24 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 15 h / 25 - 30 °C 1.2: 2 h / 0 - 10 °C 2.1: aluminum (III) chloride; sodium tetrahydroborate / Dimethyl ether / 30 h / 0 - 65 °C View Scheme | |
Multi-step reaction with 2 steps 1: aluminum (III) chloride / dichloromethane / -10 - 5 °C / Inert atmosphere 2: 1,1,3,3-Tetramethyldisiloxane / 5 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h 1.2: 1 h / 4 - 5 °C 2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 5 - 10 °C View Scheme | |
Multi-step reaction with 2 steps 1: aluminum (III) chloride / dichloromethane / 1 h / -20 - 20 °C 2: triethylsilane; boron trifluoride diethyl etherate / 1,2-dichloro-ethane; acetonitrile / 3 h / 0 - 50 °C View Scheme |
5-bromo-2-chloro-benzoyl chloride
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aluminum (III) chloride / dichloromethane / 1 h / -5 - 0 °C 2: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / -20 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: aluminum (III) chloride / dichloromethane / 1 h / Ca. -12 - Ca.-8 °C / Inert atmosphere 2: triethylsilane / dichloromethane / 0.3 h / 0 - 15 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: aluminum (III) chloride / dichloromethane / 0.5 h / 0 °C 1.2: 0 °C 2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / -10 - 20 °C View Scheme |
5-bromo-2-chlorobenzoic acid
Phenetole
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
Stage #1: 5-bromo-2-chlorobenzoic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 25 - 30℃; for 1h; Inert atmosphere; Stage #2: Phenetole With aluminum (III) chloride In dichloromethane at 0 - 5℃; for 2h; Stage #3: With triethylsilane In dichloromethane at 20 - 25℃; for 36h; Reagent/catalyst; Temperature; | 2.5 g |
4-Bromo-2-methylaniline
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: copper(l) chloride; hydrogenchloride; sodium nitrite / water; 1,4-dioxane / 3.5 h / -5 - 80 °C 2: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / chloroform / 5 h / Reflux 3: zinc(II) chloride / 6 h / 75 °C View Scheme |
o-toluidine
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 0 °C 2: copper(l) chloride; hydrogenchloride; sodium nitrite / water; 1,4-dioxane / 3.5 h / -5 - 80 °C 3: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / chloroform / 5 h / Reflux 4: zinc(II) chloride / 6 h / 75 °C View Scheme |
5-bromo-2-chlorobenzoic acid
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 10 - 30 °C 1.2: 1 h / Cooling with ice 2.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane; acetonitrile / 30 °C / Cooling with ice View Scheme |
4-hydroxy-benzaldehyde
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide; toluene / 2 h / 60 °C / Large scale 2.1: hydroxylamine hydrochloride / ethanol / 4 h / Reflux; Large scale 2.2: 5 h / Reflux; Large scale 3.1: hydrogenchloride; boron trichloride; calcium chloride / chlorobenzene / 20 h / 100 °C / Large scale 4.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale 4.2: 3 h / 20 - 80 °C / Large scale 5.1: lithium chloride; sodium tetrahydroborate / ethanol / 5 h / -5 - 70 °C / Large scale View Scheme | |
Multi-step reaction with 5 steps 1.1: potassium carbonate; tetrabutylammomium bromide / 10 h / 130 °C / Industrial scale 2.1: palladium(II) hydroxide; hydrogen / ethanol / 6 h / Reflux; Industrial scale 3.1: hydrogen fluoride / ethyl acetate / 8.5 h / Cooling with ice; Industrial scale 4.1: hydrogenchloride / water; methanol / 6 h / 80 °C / Industrial scale 5.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 °C / Industrial scale 5.2: 4 h / 20 - 80 °C / Industrial scale View Scheme |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale 1.2: 3 h / 20 - 80 °C / Large scale 2.1: lithium chloride; sodium tetrahydroborate / ethanol / 5 h / -5 - 70 °C / Large scale View Scheme |
4-ethoxybenzonitrile
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: hydrogenchloride; boron trichloride; calcium chloride / chlorobenzene / 20 h / 100 °C / Large scale 2.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale 2.2: 3 h / 20 - 80 °C / Large scale 3.1: lithium chloride; sodium tetrahydroborate / ethanol / 5 h / -5 - 70 °C / Large scale View Scheme |
4-ethoxybenzaldehyde
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: hydroxylamine hydrochloride / ethanol / 4 h / Reflux; Large scale 1.2: 5 h / Reflux; Large scale 2.1: hydrogenchloride; boron trichloride; calcium chloride / chlorobenzene / 20 h / 100 °C / Large scale 3.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale 3.2: 3 h / 20 - 80 °C / Large scale 4.1: lithium chloride; sodium tetrahydroborate / ethanol / 5 h / -5 - 70 °C / Large scale View Scheme | |
Multi-step reaction with 4 steps 1.1: palladium(II) hydroxide; hydrogen / ethanol / 6 h / Reflux; Industrial scale 2.1: hydrogen fluoride / ethyl acetate / 8.5 h / Cooling with ice; Industrial scale 3.1: hydrogenchloride / water; methanol / 6 h / 80 °C / Industrial scale 4.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 °C / Industrial scale 4.2: 4 h / 20 - 80 °C / Industrial scale View Scheme |
4-bromo-aniline
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: hydrogenchloride; boron trichloride; calcium chloride / chlorobenzene / 20 h / 100 °C / Large scale 2.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale 2.2: 3 h / 20 - 80 °C / Large scale 3.1: lithium chloride; sodium tetrahydroborate / ethanol / 5 h / -5 - 70 °C / Large scale View Scheme | |
Multi-step reaction with 4 steps 1.1: water; methanol / 5 h / 20 °C / Cooling with ice; Large scale 2.1: aluminum (III) chloride / ethyl acetate / 8 h / Cooling with ice; Reflux; Large scale 3.1: hydrogenchloride / water; methanol / 6 h / 80 °C / Large scale 4.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale 4.2: 4 h / 20 - 80 °C / Large scale View Scheme | |
Multi-step reaction with 4 steps 1.1: water; methanol / 5.5 h / 20 °C / Cooling with ice; Industrial scale 2.1: hydrogen fluoride / ethyl acetate / 8.5 h / Cooling with ice; Industrial scale 3.1: hydrogenchloride / water; methanol / 6 h / 80 °C / Industrial scale 4.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 °C / Industrial scale 4.2: 4 h / 20 - 80 °C / Industrial scale View Scheme |
p-cresol
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide; toluene / 2.5 h / 60 °C / Large scale 2.1: N-chloro-succinimide; dibenzoyl peroxide / Petroleum ether / 8 h / Reflux; Large scale 3.1: zinc(II) chloride / ethyl acetate / 8 h / Reflux; Large scale 4.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale 4.2: 3 h / 20 - 80 °C / Large scale View Scheme | |
Multi-step reaction with 5 steps 1.1: potassium carbonate; tetrabutylammomium bromide / 10 h / 130 °C / Large scale 2.1: N-Bromosuccinimide; dibenzoyl peroxide / chloroform / 6 h / Reflux; Large scale 3.1: aluminum (III) chloride / ethyl acetate / 8 h / Cooling with ice; Reflux; Large scale 4.1: hydrogenchloride / water; methanol / 6 h / 80 °C / Large scale 5.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale 5.2: 4 h / 20 - 80 °C / Large scale View Scheme |
1-ethoxy-4-methylbenzene
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: N-chloro-succinimide; dibenzoyl peroxide / Petroleum ether / 8 h / Reflux; Large scale 2.1: zinc(II) chloride / ethyl acetate / 8 h / Reflux; Large scale 3.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale 3.2: 3 h / 20 - 80 °C / Large scale View Scheme | |
Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; dibenzoyl peroxide / chloroform / 6 h / Reflux; Large scale 2.1: aluminum (III) chloride / ethyl acetate / 8 h / Cooling with ice; Reflux; Large scale 3.1: hydrogenchloride / water; methanol / 6 h / 80 °C / Large scale 4.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale 4.2: 4 h / 20 - 80 °C / Large scale View Scheme |
2-chloro-benzaldehyde
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: N-Bromosuccinimide / dichloromethane / 10.5 h / 5 °C / Large scale 2: sodium tetrahydroborate / ethanol / 4 h / 20 °C / Large scale 3: thionyl chloride / 3 h / 70 °C / Large scale 4: aluminum (III) chloride / ethyl acetate / 9 h / 78 °C / Cooling with ice; Large scale View Scheme |
2-chloro-5-bromobenzaldehyde
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium tetrahydroborate / ethanol / 4 h / 20 °C / Large scale 2: thionyl chloride / 3 h / 70 °C / Large scale 3: aluminum (III) chloride / ethyl acetate / 9 h / 78 °C / Cooling with ice; Large scale View Scheme |
5-bromo-2-chlorobenzyl alcohol
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: thionyl chloride / 3 h / 70 °C / Large scale 2: aluminum (III) chloride / ethyl acetate / 9 h / 78 °C / Cooling with ice; Large scale View Scheme |
4-ethoxybenzyl bromide
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride / ethyl acetate / 8 h / Cooling with ice; Reflux; Large scale 2.1: hydrogenchloride / water; methanol / 6 h / 80 °C / Large scale 3.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale 3.2: 4 h / 20 - 80 °C / Large scale View Scheme |
4-bromoacetanilide
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride / ethyl acetate / 8 h / Cooling with ice; Reflux; Large scale 2.1: hydrogenchloride / water; methanol / 6 h / 80 °C / Large scale 3.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale 3.2: 4 h / 20 - 80 °C / Large scale View Scheme | |
Multi-step reaction with 3 steps 1.1: hydrogen fluoride / ethyl acetate / 8.5 h / Cooling with ice; Industrial scale 2.1: hydrogenchloride / water; methanol / 6 h / 80 °C / Industrial scale 3.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 °C / Industrial scale 3.2: 4 h / 20 - 80 °C / Industrial scale View Scheme |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: hydrogenchloride / water; methanol / 6 h / 80 °C / Large scale 2.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale 2.2: 4 h / 20 - 80 °C / Large scale View Scheme | |
Multi-step reaction with 2 steps 1.1: hydrogenchloride / water; methanol / 6 h / 80 °C / Industrial scale 2.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 °C / Industrial scale 2.2: 4 h / 20 - 80 °C / Industrial scale View Scheme |
(2-chloro-5-bromophenyl)(4-fluorophenyl)methanone
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide / N,N-dimethyl-formamide / 50 - 60 °C 2: sodium tetrahydroborate / tetrahydrofuran / 0.5 h / 10 °C / Inert atmosphere View Scheme |
fluorobenzene
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 39 - 42 °C 1.2: Reflux 2.1: sodium hydroxide / N,N-dimethyl-formamide / 50 - 60 °C 3.1: sodium tetrahydroborate / tetrahydrofuran / 0.5 h / 10 °C / Inert atmosphere View Scheme |
4-ethoxybenzyl alcohol
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: hydrogen fluoride / ethyl acetate / 8.5 h / Cooling with ice; Industrial scale 2.1: hydrogenchloride / water; methanol / 6 h / 80 °C / Industrial scale 3.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 °C / Industrial scale 3.2: 4 h / 20 - 80 °C / Industrial scale View Scheme |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
4-(5-bromo-2-chlorobenzyl)phenol
Conditions | Yield |
---|---|
With boron tribromide; sodium hydrogencarbonate In dichloromethane at 20 - 30℃; for 0.5h; Inert atmosphere; | 100% |
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With boron trichloride In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: With boron tribromide In dichloromethane at 0℃; | 98% |
With boron tribromide In dichloromethane for 1h; | 95% |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane at -80 - -75℃; for 3h; Inert atmosphere; Stage #2: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -80 - -75℃; for 4h; | 100% |
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Sealed tube; Stage #2: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -78℃; for 1h; Sealed tube; |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.666667h; Inert atmosphere; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -78℃; for 5h; Inert atmosphere; | 100% |
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-hexyllithium In tetrahydrofuran; hexane; toluene at -84 - -74℃; for 1h; Large scale; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene at -74 - -15℃; for 2h; Large scale; | |
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.666667h; Inert atmosphere; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -78℃; for 5h; | |
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.666667h; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -78℃; for 5h; |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.666667h; Inert atmosphere; Stage #2: (3R,4S,5R,6R)-3,4,5-tris(trimethylsilyloxy)-6-((trimethylsilyloxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -78℃; for 5h; Inert atmosphere; | 100% |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
(3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium; isopropylmagnesium chloride In tetrahydrofuran; hexane; toluene at -30℃; for 1h; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene for 1h; | 99% |
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; toluene at -78 - -70℃; for 0.5h; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; toluene at -70℃; for 0.5h; Stage #3: With methanesulfonic acid In methanol at 20℃; for 16h; Further stages.; | 85% |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; toluene at -80 - -70℃; for 0.5h; Inert atmosphere; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; toluene at -80 - -70℃; for 1h; Stage #3: With trifluoroacetic acid In tetrahydrofuran; water; toluene at -20 - 20℃; | 98.4% |
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -80 - -78℃; for 0.5h; Inert atmosphere; Large scale; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene for 1h; Cooling; Large scale; Stage #3: With trifluoroacetic acid In tetrahydrofuran; hexane; water; toluene at -30 - 15℃; for 2h; Large scale; |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
2-chloro-N-methoxy-N-methylacetamide
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.75h; Stage #2: 2-chloro-N-methoxy-N-methylacetamide In tetrahydrofuran; hexane at -78℃; for 3h; | 98% |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
B
1-benzyl-4-ethoxybenzene
Conditions | Yield |
---|---|
With palladium on activated charcoal; hydrogen In ethanol at 20℃; for 3h; Reagent/catalyst; | A n/a B 96% |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; toluene at -78℃; for 0.5h; | 93% |
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: With ammonium chloride In tetrahydrofuran at 20℃; for 0.5h; | 93% |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
(3R,4R,6R)-3,4-bis(benzyloxy)-6-((benzyloxy)methyl)-5,5-difluorotetrahydro-2H-pyran-2-one
C42H41ClF2O6
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 1h; Inert atmosphere; Stage #2: (3R,4R,6R)-3,4-bis(benzyloxy)-6-((benzyloxy)methyl)-5,5-difluorotetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene at -98℃; for 3h; Stage #3: With water; ammonium chloride In tetrahydrofuran; hexane; toluene at -98 - 20℃; stereoselective reaction; | 91% |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
(5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; copper(II) acetate monohydrate In water at 80℃; for 8h; | 90% |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
(3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-thiopyran-2-one
2,3,4,6-tetra-O-benzyl-1-C-[4-chloro-3-(4-ethoxybenzyl)phenyl]-5-thio-D-glucopyranose
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With magnesium; ethylene dibromide In tetrahydrofuran at 20℃; Reflux; Stage #2: (3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-thiopyran-2-one In tetrahydrofuran at 20℃; for 1h; Grignard reaction; Stage #3: With ammonium chloride In tetrahydrofuran; water Saturated solution; | 89% |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 0.5h; Stage #2: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene at -78℃; | 88% |
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With isopropylmagnesium chloride In tetrahydrofuran at -5 - 0℃; for 1h; Inert atmosphere; Stage #2: C19H25NO6 In tetrahydrofuran at 25 - 30℃; Inert atmosphere; | 88% |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
2,3,4,5,6-penta-O-benzyl aldehydo D-glucose
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane at -70℃; for 1h; Stage #2: 2,3,4,5,6-penta-O-benzyl-aldehydo-D-glucose In tetrahydrofuran; hexane at -70℃; for 2h; Stage #3: With water In tetrahydrofuran; hexane at -70 - 20℃; for 20h; | 87.1% |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
2,3,4,6-Tetra-O-benzyl-D-glucopyranose
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With iodine; magnesium In tetrahydrofuran at 60℃; for 1h; Stage #2: 2,3,4,6-Tetra-O-benzyl-D-glucopyranose With isopropylmagnesium bromide In tetrahydrofuran at 0 - 60℃; for 2h; | 87% |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
((3aS,5R,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(morpholin-4-yl)methanone
(4-chloro-3-(4-ethoxybenzyl)phenyl)((3aS,5R,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuran[2,3-d][1,3]dioxolan-5-yl)methanone
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran at -80 - -70℃; for 1h; Stage #2: ((3aS,5R,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(morpholin-4-yl)methanone In tetrahydrofuran at -80 - 0℃; | 86.3% |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
(4R,5S,6R)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-2-cyclohexen-1-one
C50H49ClO6
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With magnesium; ethylene dibromide In tetrahydrofuran for 1h; Inert atmosphere; Reflux; Stage #2: (4R,5S,6R)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-2-cyclohexen-1-one In tetrahydrofuran at 25℃; for 3h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; water | 86% |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With isopropylmagnesium chloride In tetrahydrofuran at -5 - 0℃; for 2h; Stage #2: 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide With N,N,N,N,-tetramethylethylenediamine; isopropylmagnesium chloride; cobalt(II) chloride In tetrahydrofuran; 2-methyltetrahydrofuran at 0 - 30℃; for 2.5h; Reagent/catalyst; Solvent; | 84% |
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; acetone at -78℃; for 1h; Inert atmosphere; Stage #2: 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide With copper(l) iodide In tetrahydrofuran at -40 - -30℃; for 1h; Reagent/catalyst; Temperature; |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
acetic anhydride
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With magnesium; methyl iodide In tetrahydrofuran for 1h; Reflux; Stage #2: acetic anhydride In tetrahydrofuran at -20 - 20℃; for 3h; | 84% |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
allyl alcohol
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -80 - -70℃; for 1h; Stage #2: 3,4,5-tris[(trimethylsilyl)oxy]-6-{[(trimethylsilyl)oxy]methyl}-tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene at -80 - -70℃; Stage #3: allyl alcohol With methanesulfonic acid In tetrahydrofuran; hexane; toluene at -80 - -20℃; | 83% |
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -80 - -70℃; for 1h; Stage #2: 3,4,5-tris[(trimethylsilyl)oxy]-6-{[(trimethylsilyl)oxy]methyl}-tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene at -80 - -70℃; Stage #3: allyl alcohol With methanesulfonic acid In tetrahydrofuran; hexane; toluene at -80 - 20℃; |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
(2R,3S,4S)-2,3,4-tris(benzyloxy)-4-(4-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methylpiperazin-1-yl)butan-1-one
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With isopropylmagnesium chloride In tetrahydrofuran at -5 - 0℃; for 1h; Inert atmosphere; Stage #2: (2R,3S,4S)-2,3,4-tris(benzyloxy)-4-(4-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methylpiperazin-1-yl)butan-1-one In tetrahydrofuran at 20 - 30℃; Inert atmosphere; | 83% |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane; toluene at -78 - -65℃; for 2h; Inert atmosphere; | 78.6% |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78 - -68℃; for 1h; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; n-heptane; cyclohexane at -78 - -68℃; for 30h; | 78.3% |
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 1h; Large scale; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 3h; Large scale; | 78% |
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 1h; Inert atmosphere; Industrial scale; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one With methanesulfonic acid In tetrahydrofuran; methanol; hexane; toluene at -78 - 40℃; for 14h; Industrial scale; | 78% |
Multi-step reaction with 2 steps 1.1: N,N,N',N'',N'''-pentamethyldiethylenetriamine; n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: 2 h / -78 °C / Inert atmosphere 2.1: methanol / 10 h / 20 °C View Scheme |
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
methanesulfonic acid
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 1h; Inert atmosphere; Large scale; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene at -78℃; for 3h; Large scale; Stage #3: methanesulfonic acid In methanol at 0 - 40℃; for 11h; Large scale; | 78% |
(4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-one
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 0.5h; Stage #2: (4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene at -78℃; for 0.5h; | 78% |
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