Conditions | Yield |
---|---|
With triphenylphosphine In dichloromethane; hexane-diethyl ether | 100% |
4-phenyl-butan-1-ol
1-Bromo-4-phenylbutane
Conditions | Yield |
---|---|
With hydrogen bromide for 12h; Reagent/catalyst; Irradiation; Reflux; | 99.6% |
With allyl bromide; 1,1'-carbonyldiimidazole In acetonitrile for 1h; Heating; | 98% |
With carbon tetrabromide; triphenylphosphine In dichloromethane at 25℃; | 95% |
N-methyl-N-[4-(diphenylphosphino)benzyl]pyrrolidinium bromide
4-phenyl-butan-1-ol
A
Br(1-)*C24H27NOP(1+)
B
1-Bromo-4-phenylbutane
Conditions | Yield |
---|---|
With carbon tetrabromide In 1,2-dichloro-ethane at 40℃; for 2h; | A n/a B 97% |
4-Phenylbutyric acid
1-Bromo-4-phenylbutane
Conditions | Yield |
---|---|
With trimethylsilyl bromide; 1,1,3,3-Tetramethyldisiloxane; indium tribromide In chloroform at 60℃; for 4h; Sealed tube; Inert atmosphere; | 97% |
With indium(III) bromide; 1,1,3,3-Tetramethyldisiloxane; trimethylsilyl cyanide In chloroform at 60℃; Inert atmosphere; | |
Multi-step reaction with 2 steps 1: dimethylsulfide borane complex / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 2: triphenylphosphine; carbon tetrabromide / acetonitrile / 3 h / 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: dimethylsulfide borane complex / tetrahydrofuran / 2 h / 20 °C 2: triphenylphosphine; carbon tetrabromide / acetonitrile / 3 h / 20 °C View Scheme |
(4-bromo-1-buten-1-yl)benzene
1-Bromo-4-phenylbutane
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In ethanol; water under 225.023 Torr; for 5h; | 93% |
4-(diphenylphosphino)-benzyltrimethylammonium bromide
4-phenyl-butan-1-ol
A
Br(1-)*C22H25NOP(1+)
B
1-Bromo-4-phenylbutane
Conditions | Yield |
---|---|
With carbon tetrabromide In 1,2-dichloro-ethane at 60℃; for 2h; | A n/a B 91% |
Conditions | Yield |
---|---|
at 5℃; for 2h; Temperature; | 85.8% |
Conditions | Yield |
---|---|
With copper(I) bromide; lithium bromide In tetrahydrofuran at 50 - 55℃; for 1h; | 85% |
benzenediazonium tetrafluoroborate
4-bromo-1-butylboronic acid catechol ester
1-Bromo-4-phenylbutane
Conditions | Yield |
---|---|
With 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride; palladium diacetate In tetrahydrofuran at 20℃; for 4.5h; Sizuki-Miyaura cross coupling; | 61% |
4-phenyl-butan-1-ol
triphenylphosphine
A
1-Bromo-4-phenylbutane
B
Triphenylphosphine oxide
Conditions | Yield |
---|---|
With carbon tetrabromide In 1,2-dichloro-ethane | A 53% B n/a |
5-Phenylpentanoic acid
1-Bromo-4-phenylbutane
Conditions | Yield |
---|---|
With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; caesium carbonate; Diethyl 2-bromomalonate In chlorobenzene at 20℃; for 4h; Inert atmosphere; Irradiation; | 45% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 95℃; for 23h; | A 11% B 21% C 44% D 3% |
With rubidium carbonate In N,N-dimethyl-formamide at 95℃; for 23h; Product distribution; other reag; | A 12% B 34% C 20% D 18% |
Conditions | Yield |
---|---|
With n-butyllithium In diethyl ether; hexane for 2h; Heating; | 42% |
2-phenylbut-2-ene
1-Bromo-4-phenylbutane
Conditions | Yield |
---|---|
With hydrogen bromide; dihydrogen peroxide |
Conditions | Yield |
---|---|
Multistep reaction; |
4-phenylbutyl acetate
1-Bromo-4-phenylbutane
Conditions | Yield |
---|---|
With hydrogen bromide Heating; Yield given; |
Conditions | Yield |
---|---|
Anlagerung von HBr; |
1-Bromo-4-phenylbutane
Conditions | Yield |
---|---|
With hydrogen bromide at 130 - 140℃; im Rohr; |
benzylmagnesium chloride
1-Bromo-4-phenylbutane
Conditions | Yield |
---|---|
With diethyl ether |
4-phenyl-but-3-yn-1-ol
1-Bromo-4-phenylbutane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: H2 / Pd-CaCO3 2: PBr3 View Scheme |
phenylacetylene
1-Bromo-4-phenylbutane
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: (i) EtMgBr, (ii) /BRN= 102378/ 2: H2 / Pd-CaCO3 3: PBr3 View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 79 percent / LiAlH4 2: 61 percent / PBr3 View Scheme |
methyl 3-(benzyl)propanoate
1-Bromo-4-phenylbutane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: LAH 2: PBr3 View Scheme | |
Multi-step reaction with 2 steps 1: LiAlH4 / diethyl ether 2: (i) TsCl, Py, Et2O, (ii) LiBr, acetone View Scheme |
ethyl 4-phenylbutyrate
1-Bromo-4-phenylbutane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium; alcohol 2: fuming hydrobromic acid / 100 °C View Scheme |
3-phenylpropylmagnesium bromide
1-Bromo-4-phenylbutane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: fuming hydrobromic acid / 100 °C View Scheme | |
Multi-step reaction with 2 steps 2: phosphorus pentabromide View Scheme |
1-phenyl-2-bromoethane
1-Bromo-4-phenylbutane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: (i) Mg, Et2O, (ii) /BRN= 102378/ 2: HBr / benzene View Scheme | |
Multi-step reaction with 2 steps 2: aq. HBr, aq. H2SO4 View Scheme | |
Multi-step reaction with 2 steps 1: Mg / diethyl ether 2: PBr3 View Scheme |
4-phenyl-butan-1-ol
A
1-Bromo-4-phenylbutane
B
4-(Bromobutyl)benzene
Conditions | Yield |
---|---|
With phosphorus tribromide; sodium hydrogencarbonate In 1,4-dioxane; n-heptane; water; ethyl acetate |
p-imidazo-1-ylphenol
1-Bromo-4-phenylbutane
Conditions | Yield |
---|---|
With NaH In N,N-dimethyl-formamide |
1-Bromo-4-phenylbutane
1-(4-azidobutyl)benzene
Conditions | Yield |
---|---|
With sodium azide In N,N-dimethyl-formamide at 80℃; | 100% |
With sodium azide In N,N-dimethyl-formamide at 70℃; for 9h; Inert atmosphere; | 99% |
With sodium azide In dimethyl sulfoxide at 20℃; for 36h; | 85% |
1-Bromo-4-phenylbutane
trimethyl(difluoromethyl)silane
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; copper(l) iodide; cesium fluoride; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 50℃; for 6h; Inert atmosphere; Glovebox; Schlenk technique; | 100% |
1-Bromo-4-phenylbutane
triphenylphosphine
(4-phenylbut-1-yl)triphenylphosphonium bromide
Conditions | Yield |
---|---|
In toluene Reflux; | 99% |
In toluene at 110℃; for 20h; Inert atmosphere; | 63% |
In toluene Heating; |
1-Bromo-4-phenylbutane
4'-hydroxy-3-biphenylcarbonitrile
4'-(4-phenylbutoxy)-[1,1'-biphenyl]-3-carbonitrile
Conditions | Yield |
---|---|
With potassium carbonate at 20 - 40℃; Inert atmosphere; | 99% |
1-Bromo-4-phenylbutane
methyl 3-hydroxybenzoate
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide for 12h; Williamson Ether Synthesis; Inert atmosphere; Reflux; | 99% |
1-Bromo-4-phenylbutane
isopropylamine
N-isopropyl-4-phenylbutan-1-amine
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 24h; | 99% |
1-Bromo-4-phenylbutane
A
polymer, CH2Cl2-insoluble; monomer(s): 1-bromo-4-phenylbutane; 5-(4-(4-ethenylphenyl)butoxy)methyl-1,3-dithiane, 1 molar part; styrene, 19 molar partspolymer, CH2Cl2-insoluble; monomer(s): 1-bromo-4-phenylbutane; 5-(4-(4-ethenylphenyl)butoxy)methyl-1,3-dithiane, 1 molar part; styrene, 19 molar parts
Conditions | Yield |
---|---|
Stage #1: polymer; monomer(s): 5-(4-(4-ethenylphenyl)butoxy)methyl-1,3-dithiane, 5 mol percent; styrene, 95 mol percent With n-butyllithium In tetrahydrofuran; hexane at -40 - -30℃; Stage #2: 1-Bromo-4-phenylbutane In tetrahydrofuran; hexane at -30 - -10℃; | A 0.7% B 98.9% |
1-Bromo-4-phenylbutane
methyl 4-hydroxylbenzoate
4-(4-phenyl-1-butoxy)benzoic acid
Conditions | Yield |
---|---|
Stage #1: 1-Bromo-4-phenylbutane; methyl 4-hydroxylbenzoate With potassium carbonate In N,N-dimethyl-formamide at 115℃; for 11h; Stage #2: With water; sodium hydroxide In ethanol for 3h; Reflux; Stage #3: With hydrogenchloride In ethanol; water pH=2; Reagent/catalyst; Concentration; | 98.7% |
1-Bromo-4-phenylbutane
sodium 4-phenylbutane-1-sulfonate
Conditions | Yield |
---|---|
With sodium sulfite In water for 24h; Heating; | 96% |
With sodium sulfite In tetrahydrofuran; ethanol; water at 160℃; for 0.25h; Microwave irradiation; |
1-Bromo-4-phenylbutane
N-benzylidene-4-fluoroaniline
Conditions | Yield |
---|---|
Stage #1: 1-Bromo-4-phenylbutane With lithium In diethyl ether at -40 - 0℃; for 2h; Inert atmosphere; Stage #2: N-benzylidene-4-fluoroaniline In diethyl ether at -78 - 20℃; for 3h; Inert atmosphere; | 96% |
1-Bromo-4-phenylbutane
4-methoxy-N-[(3-methoxyphenyl)methylene]benzenamine
Conditions | Yield |
---|---|
Stage #1: 1-Bromo-4-phenylbutane With lithium In diethyl ether at -40 - 0℃; for 2h; Inert atmosphere; Stage #2: 4-methoxy-N-[(3-methoxyphenyl)methylene]benzenamine In diethyl ether at -78 - 20℃; for 3h; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In acetonitrile for 18h; Reflux; | 93% |
Conditions | Yield |
---|---|
With 6,6'-dimethyl-2,2'-bipyridine; nickel(II) bromide trihydrate; di-tert-butyl dicarbonate; sodium iodide; magnesium chloride; zinc In N,N-dimethyl acetamide at 30℃; for 24h; regioselective reaction; | 93% |
1-Bromo-4-phenylbutane
3,4-dihydroxybenzaldehyde
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; | 93% |
1-Bromo-4-phenylbutane
Conditions | Yield |
---|---|
Stage #1: 1-Bromo-4-phenylbutane With lithium In diethyl ether at -40 - 0℃; for 2h; Inert atmosphere; Stage #2: N-(3-methylbenzylidene)-4-methoxybenzenamine In diethyl ether at -78 - 20℃; for 3h; Inert atmosphere; | 93% |
1-Bromo-4-phenylbutane
(3S)-1-(pent-4-enyl)-[(1R)-hydroxyethyl]azetidin-2-one
(3S)-1-(pent-4-enyl)-[(1R)-(4-phenylbutoxy)ethyl]azetidin-2-one
Conditions | Yield |
---|---|
Stage #1: (3S)-1-(pent-4-enyl)-[(1R)-hydroxyethyl]azetidin-2-one With sodium hydride In N,N-dimethyl-formamide at 0℃; Inert atmosphere; Stage #2: 1-Bromo-4-phenylbutane With potassium iodide In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; | 92% |
1-Bromo-4-phenylbutane
Conditions | Yield |
---|---|
Stage #1: tert-butyl (R)-3-(3-(4-(1-(hydroxyimino)ethyl)phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboxylate With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 1-Bromo-4-phenylbutane In tetrahydrofuran for 16h; Reflux; | 92% |
1-Bromo-4-phenylbutane
1,4,7,10-tetraoxa-15-azacyclopentadecane
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 80℃; for 20h; | 91.4% |
1-Bromo-4-phenylbutane
(3S)-1-(4-methoxybenzyl)-[(1R)-hydroxyethyl]azetidin-2-one
(3S)-1-(4-methoxybenzyl)-[(1R)-(4-phenylbutoxy)ethyl]azetidin-2-one
Conditions | Yield |
---|---|
Stage #1: (3S)-1-(4-methoxybenzyl)-[(1R)-hydroxyethyl]azetidin-2-one With sodium hydride In N,N-dimethyl-formamide at 0℃; Inert atmosphere; Stage #2: 1-Bromo-4-phenylbutane With potassium iodide In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; | 91% |
1-Bromo-4-phenylbutane
mercaptoacetic acid
((4-phenylbutyl)sulfanyl)acetic acid
Conditions | Yield |
---|---|
With sodium hydroxide In methanol at 20℃; | 91% |
2-pyrrolidinon
1-Bromo-4-phenylbutane
1-[4-phenylbutyl]pyrrolidin-2-one
Conditions | Yield |
---|---|
Stage #1: 2-pyrrolidinon With sodium hydride In toluene; paraffin oil for 10h; Inert atmosphere; Reflux; Stage #2: 1-Bromo-4-phenylbutane In 5,5-dimethyl-1,3-cyclohexadiene; toluene; paraffin oil for 4h; Inert atmosphere; Reflux; | 91% |
Conditions | Yield |
---|---|
With 6,6'-dimethyl-2,2'-bipyridine; nickel(II) bromide trihydrate; di-tert-butyl dicarbonate; sodium iodide; magnesium chloride; zinc In N,N-dimethyl acetamide at 30℃; for 24h; regioselective reaction; | 91% |
1-Bromo-4-phenylbutane
Methyl thioglycolate
methyl 2-[(4-phenylbutyl)thio]acetate
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide; acetone at 25℃; for 30h; | 90% |
With potassium carbonate In dimethyl sulfoxide; acetone at 25℃; for 30h; | 90% |
Stage #1: Methyl thioglycolate With potassium carbonate In acetone for 0.25h; Stage #2: 1-Bromo-4-phenylbutane In acetone for 21h; Reflux; |
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