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potassium tert-butylate
4-chlorobenzoyl chloride
tert-butyl-4-bromobenzoate
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; | 100% |
In diethyl ether for 1h; Substitution; | 95% |
In tetrahydrofuran at -78 - 20℃; for 2h; | 95% |
1.4-dibromobenzene
di-tert-butyl dicarbonate
tert-butyl-4-bromobenzoate
Conditions | Yield |
---|---|
Stage #1: 1.4-dibromobenzene With n-butyllithium; butyl magnesium bromide In tetrahydrofuran; hexane; toluene at -5℃; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; hexane; toluene at -5℃; Stage #3: With citric acid In tetrahydrofuran; hexane; toluene Further stages.; | 98% |
Stage #1: 1.4-dibromobenzene With n-butyllithium; butyl magnesium bromide In tetrahydrofuran; hexane; toluene at -5℃; for 1h; Inert atmosphere; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; hexane; toluene at -5℃; for 2h; Inert atmosphere; | 98% |
di-tert-butyl peroxide
4-bromo-benzaldehyde
tert-butyl-4-bromobenzoate
Conditions | Yield |
---|---|
With copper(I) bromide In hexane at 50℃; for 5h; Inert atmosphere; | 89% |
Conditions | Yield |
---|---|
Stage #1: 4-Bromobenzoic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 25℃; Stage #2: potassium tert-butylate In tetrahydrofuran at 25℃; for 2h; | 89% |
tert.-butylhydroperoxide
4-Bromophenylacetonitrile
tert-butyl-4-bromobenzoate
Conditions | Yield |
---|---|
With Zr6(μ3-O)4(μ3-OH)4(OH)6(H2O)6(IDA)3; potassium hydroxide In acetonitrile at 80℃; for 10h; | 87% |
In water; acetonitrile at 60℃; for 16h; Molecular sieve; Schlenk technique; Inert atmosphere; | 83% |
Conditions | Yield |
---|---|
With 1H-imidazole; tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In water at 80℃; for 7h; Green chemistry; chemoselective reaction; | 87% |
carbon monoxide
4-bromo-aniline
tert-butyl alcohol
tert-butyl-4-bromobenzoate
Conditions | Yield |
---|---|
Stage #1: 4-bromo-aniline With tetrafluoroboric acid; acetic acid; isopentyl nitrite In water at 20℃; for 0.0833333h; Stage #2: carbon monoxide; tert-butyl alcohol With Eosin Y at 18℃; under 37503.8 Torr; for 4h; Inert atmosphere; Darkness; Irradiation; | 79% |
Stage #1: 4-bromo-aniline With tetrafluoroboric acid; sodium nitrite In water at 0℃; for 0.75h; Stage #2: carbon monoxide; tert-butyl alcohol With sodium formate In acetonitrile at 20℃; under 37503.8 Torr; for 3h; | 146.6 mg |
Conditions | Yield |
---|---|
With pyridine In dichloromethane for 48h; Ambient temperature; | 78% |
With pyridine In dichloromethane for 48h; | 70% |
With n-butyllithium In diethyl ether; hexane Ambient temperature; | |
With pyridine In dichloromethane | 8.9 g (70%) |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 2h; Inert atmosphere; | 66% |
4-Bromobenzoic acid
di-tert-butyl dicarbonate
tert-butyl-4-bromobenzoate
Conditions | Yield |
---|---|
With dmap In tert-butyl alcohol at 40℃; | 63% |
With dmap In tert-butyl alcohol at 20℃; for 12h; Concentration; Time; | 62% |
With dmap In tert-butyl alcohol at 20℃; for 12h; Concentration; | 62% |
With dmap In tert-butyl alcohol at 50℃; | 21% |
Conditions | Yield |
---|---|
With dmap; di-tert-butyl dicarbonate at 20℃; for 12h; | 62% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 20℃; for 18h; | 55% |
With dmap; diisopropyl-carbodiimide In dichloromethane at 35℃; for 5h; | 49 g |
N-tert-butoxy-4-chlorobenzamide
tert-butyl-4-bromobenzoate
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid; copper(ll) bromide In 1,4-dioxane at 70℃; for 3h; | 51% |
With N-Bromosuccinimide In toluene at 80℃; for 1h; | 50% |
4-methoxycarbonylphenyl bromide
sodium t-butanolate
tert-butyl-4-bromobenzoate
Conditions | Yield |
---|---|
In toluene at 80℃; for 0.25h; transesterification; |
4-Bromobenzoic acid
tert-butyl-4-bromobenzoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 3 h / 43 °C / Inert atmosphere 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 48 h / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: thionyl chloride; N,N-dimethyl-formamide / 1 h / Reflux 2: tetrahydrofuran / 1 h / 0 - 5 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: thionyl chloride; N,N-dimethyl-formamide / 3 h / 60 °C 2.1: potassium carbonate / ethyl acetate; water 2.2: 4 h / 0 - 20 °C 3.1: N-Bromosuccinimide / toluene / 1 h / 80 °C View Scheme | |
Multi-step reaction with 2 steps 1: thionyl chloride; N,N-dimethyl-formamide / 1 h / Inert atmosphere; Reflux; Schlenk technique 2: tetrahydrofuran / 0 °C View Scheme |
N-(4-bromobenzoyl)imidazole
tert-butyl alcohol
tert-butyl-4-bromobenzoate
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 48h; Inert atmosphere; | 2.15 g |
4-chlorobenzoyl chloride
tert-butyl-4-bromobenzoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate / ethyl acetate; water 1.2: 4 h / 0 - 20 °C 2.1: N-Bromosuccinimide / toluene / 1 h / 80 °C View Scheme |
tert.-butylhydroperoxide
4-bromo-benzaldehyde
tert-butyl-4-bromobenzoate
Conditions | Yield |
---|---|
With 1,2,3-Benzotriazole; potassium iodide In water; 1,2-dichloro-ethane at 100℃; for 12h; High pressure; |
4-Bromophenylacetonitrile
tert-butyl-4-bromobenzoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: C56H53ClN3P2Ru(1+)*F6P(1-); tert.-butylhydroperoxide / benzene / 18 h / 40 °C / Inert atmosphere 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 20 °C / Inert atmosphere View Scheme |
tert-butyl-4-bromobenzoate
benzoic acid tert-butyl ester
Conditions | Yield |
---|---|
Stage #1: tert-butyl-4-bromobenzoate With sec.-butyllithium In tetrahydrofuran; hexane; cyclohexane at -58℃; for 0.000105556h; Stage #2: With tert-butyl alcohol In tetrahydrofuran; hexane; cyclohexane at -58℃; for 0.000638889h; | 99% |
tert-butyl-4-bromobenzoate
(1,5-anhydro-2-deoxy-4,6-O-bis(tert-butylsilylidene)-3-O-triisopropylsilyl-D-arabino-hex-1-enitol)boronic acid pinacol ester
4-(1,5-anhydro-2-deoxy-4,6-O-di(tert-butyl)silanediyl-3-O-triisopropylsilyl-D-arabino-hex-1-enitolyl)benzoic acid tert-butyl ester
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; water for 4h; Reflux; | 99% |
tert-butyl-4-bromobenzoate
bis(pinacol)diborane
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; potassium acetate In 1,4-dioxane at 80℃; for 4.5h; Inert atmosphere; | 98% |
With meso-tetra(p-tolyl)porphinato-palladium(II); potassium acetate In 1,4-dioxane at 110℃; for 6h; Miyaura Borylation Reaction; chemoselective reaction; | 85% |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane Inert atmosphere; Reflux; Schlenk technique; | 80% |
1,3,4-oxathiazinane 3,3-dioxide
tert-butyl-4-bromobenzoate
tert-butyl 4-(3,3-dioxido-1,3,4-oxathiazinan-4-yl)benzoate
Conditions | Yield |
---|---|
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 2h; Buchwald-Hartwig Coupling; Inert atmosphere; Microwave irradiation; | 98% |
tert-butyl-4-bromobenzoate
4-bromo-2-iodo-benzoic acid tert-butyl ester
Conditions | Yield |
---|---|
Stage #1: tert-butyl-4-bromobenzoate In tetrahydrofuran; hexane; pentane at 20℃; for 3h; Stage #2: With iodine In tetrahydrofuran; hexane; pentane at 20℃; for 1h; Further stages.; | 97% |
Stage #1: tert-butyl-4-bromobenzoate In tetrahydrofuran at -20℃; for 1h; Stage #2: With iodine In tetrahydrofuran at 0 - 25℃; Further stages.; | 71% |
Conditions | Yield |
---|---|
With chloro(2’-amino-1,1’-biphenyl-2-yl)palladium(II) dimer; C60H54NO5P; sodium hydride In toluene at 80℃; for 12h; Inert atmosphere; enantioselective reaction; | 97% |
tert-butyl-4-bromobenzoate
carbamic acid 2-trimethylsilylethyl ester
4-(2-trimethylsilanylethoxycarbonylamino)benzoic acid tert-butyl ester
Conditions | Yield |
---|---|
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 15h; Inert atmosphere; Sealed; | 96% |
Conditions | Yield |
---|---|
With tributyl-amine; palladium diacetate; tris-(o-tolyl)phosphine In N,N-dimethyl acetamide at 100℃; | 96% |
dibenzoazepine
tert-butyl-4-bromobenzoate
Conditions | Yield |
---|---|
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 80℃; for 16h; Inert atmosphere; | 94% |
tert-butyl-4-bromobenzoate
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 105℃; | 94% |
4-(2-amino-2-methyl-propoxy)-phenylamine
tert-butyl-4-bromobenzoate
Conditions | Yield |
---|---|
With [(π-cinnamyl)Pd(tBuXPhos)]OTf In water at 45℃; for 20h; | 94% |
tert-butyl-4-bromobenzoate
phenyl trimethylsiloxane
biphenyl-4-carboxylic acid t-butyl ester
Conditions | Yield |
---|---|
With potassium fluoride; propylene glycol; chloro-[2-(9-phenyl-1,10-phenanthrolin-2-yl)phenyl]palladium In dichloromethane at 100℃; for 12h; Hiyama Coupling; Inert atmosphere; | 94% |
tert-butyl-4-bromobenzoate
benzylamine
N-benzyl-4,4'-di-tert-butylcarboxydiphenylamine
Conditions | Yield |
---|---|
With tri-tert-butyl phosphine; sodium t-butanolate; palladium diacetate In toluene at 50℃; for 17h; | 93% |
tert-butyl-4-bromobenzoate
Conditions | Yield |
---|---|
tri(tert-butyl)phosphine palladium complex In toluene at 50℃; for 12h; | 93% |
tert-butyl-4-bromobenzoate
N,N-di(4-(tert-butyl)benzoate)phenylamine
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butylphosphonium tetrafluoroborate; potassium tert-butylate In toluene at 20℃; for 2h; | 93% |
With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 80℃; for 1h; | 90% |
tert-butyl-4-bromobenzoate
sodium (Z)-2-buten-1-yl-diethylsilanolate
4-(1-methyl-2-propen-1-yl)benzoic acid, 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
With dicyclohexyl(1,1-dimethylethyl)phosphine-trihydridoboron; bis(dibenzylideneacetone)-palladium(0) In toluene at 22 - 70℃; Inert atmosphere; Sealed tube; | 91% |
3-benzyl-3H-quinazolin-4-one
tert-butyl-4-bromobenzoate
Conditions | Yield |
---|---|
Stage #1: 3-benzyl-3H-quinazolin-4-one With copper(l) iodide; lithium tert-butoxide In N,N-dimethyl-formamide at 120℃; for 0.166667h; Microwave irradiation; Inert atmosphere; Sealed tube; Stage #2: tert-butyl-4-bromobenzoate With palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide at 60 - 120℃; for 0.5h; Inert atmosphere; Microwave irradiation; Sealed tube; regiospecific reaction; | 90% |
Conditions | Yield |
---|---|
With [(π-cinnamyl)Pd(tBuXPhos)]OTf In water at 45℃; for 26h; | 90% |
1-bromo-4-methoxy-benzene
tert-butyl-4-bromobenzoate
4-tert-butoxycarbonyl-4'-methoxy-1,1'-biphenyl
Conditions | Yield |
---|---|
Stage #1: tert-butyl-4-bromobenzoate With chloro-trimethyl-silane; magnesium; ethylene dibromide; lithium chloride In tetrahydrofuran at 25℃; for 1h; Inert atmosphere; Stage #2: 1-bromo-4-methoxy-benzene With 1,1'-bis-(diphenylphosphino)ferrocene; caesium carbonate; palladium dichloride In ethanol; N,N-dimethyl-formamide at 65℃; for 12h; Suzuki-Miyaura cross coupling reaction; Inert atmosphere; | 89% |
tert-butyl-4-bromobenzoate
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 105℃; | 89% |
bromochlorobenzene
tert-butyl-4-bromobenzoate
2-allyl-5-methoxy-phenylamine
Conditions | Yield |
---|---|
Stage #1: bromochlorobenzene; 2-allyl-5-methoxy-phenylamine With tris(dibenzylideneacetone)dipalladium (0); johnphos; sodium t-butanolate In toluene at 80℃; Stage #2: tert-butyl-4-bromobenzoate With bis[2-(diphenylphosphino)phenyl] ether In toluene at 105℃; | 88% |
Conditions | Yield |
---|---|
Stage #1: tert-butyl-4-bromobenzoate With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; TurboGrignard In tetrahydrofuran at -10℃; for 24h; Stage #2: allyl bromide With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone In tetrahydrofuran at 0℃; for 1h; | 88% |
tert-butyl-4-bromobenzoate
4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane
Conditions | Yield |
---|---|
With trans-bis(triphenylphosphine)palladium dichloride; sodium carbonate In 1,4-dioxane; water at 90℃; for 18h; Inert atmosphere; | 87.5% |
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane at 90℃; for 18h; Inert atmosphere; | 87.5% |
tert-butyl-4-bromobenzoate
butyl[2-(2-hydroxyprop-2-yl)phenyl]diisopropylsilane
A
3,3-dimethyl-1,1-diisopropyl-1,3-dihydrobenzo[c][1,2]oxasilole
B
4-butylbenzoic acid t-butyl ester
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; potassium phosphate; bis(1,1,1,5,5,5-hexafluoropentane-2,4-dionato)copper(II) monohydrate; palladium diacetate In tetrahydrofuran at 100℃; for 1h; Inert atmosphere; | A 94 %Chromat. B 87% |
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