Conditions | Yield |
---|---|
With hydrogen bromide; acetic acid In dimethyl sulfoxide at 20℃; for 2h; | 100% |
With Oxone; potassium bromide In methanol at 20℃; for 4h; | 99% |
With N-Bromosuccinimide; sulfonic acid functionalized silica In diethyl ether; acetonitrile at 20℃; for 0.166667h; | 99% |
2-bromo-4-methylanisole
2-bromo-p-cresol
Conditions | Yield |
---|---|
Stage #1: 2-bromo-4-methylanisole With boron tribromide In dichloromethane at -78 - 20℃; Inert atmosphere; Stage #2: With water; sodium hydrogencarbonate In dichloromethane Inert atmosphere; | 99% |
With boron tribromide In dichloromethane at -78 - 20℃; for 2h; |
1-(methoxymethoxy)-4-methylbenzene
2-bromo-p-cresol
Conditions | Yield |
---|---|
With tris(2,2'-bipyridyl)ruthenium dichloride; carbon tetrabromide In acetonitrile at 20℃; Irradiation; | 97% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; bromine In dichloromethane at 0℃; for 8h; | A 96% B 0.9% |
Stage #1: p-cresol With toluene-4-sulfonic acid In methanol for 0.166667h; Stage #2: With N-Bromosuccinimide In methanol for 0.416667h; | A 92% B n/a |
With bromine In 1,2-dichloro-ethane at 20 - 25℃; for 7h; | A n/a B 90% |
Conditions | Yield |
---|---|
With bromine In various solvent(s) other reaction time; | A n/a B 90% |
With trifluorormethanesulfonic acid; bromine In various solvent(s) for 0.166667h; Product distribution; Mechanism; other reaction time; | A 40% B 60% |
With bromine In various solvent(s) for 0.166667h; other reaction time; | A 40% B 60% |
Conditions | Yield |
---|---|
With wild type cytochrome P450 CYP102A1 variants RLYF/A330P; oxygen; NADPH Reagent/catalyst; Enzymatic reaction; | A 14% B 82% |
With water; lithium perchlorate; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile for 48h; Irradiation; Inert atmosphere; Electrolysis; Overall yield = 50 percent; Overall yield = 37.4 mg; chemoselective reaction; |
trimethyl(4-methylphenoxy)silane
2-bromo-p-cresol
Conditions | Yield |
---|---|
With tris(2,2'-bipyridyl)ruthenium dichloride; carbon tetrabromide In acetonitrile at 20℃; Irradiation; | 69% |
Conditions | Yield |
---|---|
With diethyl dibromomalonate at 100℃; for 48h; Bromination; aromatization; | 51% |
Conditions | Yield |
---|---|
With sulfuric acid Diazotization.Eintragen der Diazoniumsalz-Loesung in ein Gemisch von wss. H2SO4 und Na2SO4 bei 130-135grad; | |
Diazotization.Einleiten von Wasserdampf in die Diazoniumsalzloesung; |
(2-Brom-4-methylphenyl)-benzoat
2-bromo-p-cresol
Conditions | Yield |
---|---|
With potassium hydroxide |
sodium 4-methylphenoxide
A
2-bromo-p-cresol
B
3,5-dibromo-4-hydroxytoluene
Conditions | Yield |
---|---|
With carbon disulfide; bromine |
p-cresol
A
2-bromo-p-cresol
B
3,5-dibromo-4-hydroxytoluene
C
3-bromo-p-cresol
D
2,5-dibromo-p-cresol
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid; bromine for 0.333333h; | A 84 % Chromat. B 3 % Chromat. C 1 % Chromat. D 1 % Chromat. |
p-cresol
A
2-bromo-p-cresol
B
3,5-dibromo-4-hydroxytoluene
C
3-bromo-p-cresol
D
2,5-dibromo-p-cresol
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid; bromine for 0.333333h; Product distribution; further reaction times; | A 24 % Chromat. B 10 % Chromat. C 18 % Chromat. D 16 % Chromat. E 1 % Chromat. |
p-cresol
A
2-bromo-p-cresol
B
3,5-dibromo-4-hydroxytoluene
C
3-bromo-p-cresol
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid; bromine for 0.333333h; Further byproducts given; | A 24 % Chromat. B 10 % Chromat. C 18 % Chromat. D 2 % Chromat. |
p-cresol
A
2-bromo-p-cresol
B
3-bromo-p-cresol
C
2,5-dibromo-p-cresol
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid; bromine for 0.333333h; Further byproducts given; | A 8 % Chromat. B 61 % Chromat. C 15 % Chromat. D 2 % Chromat. |
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid Product distribution; |
2-bromo-p-cresol
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid; zinc |
2-bromo-p-cresol
Conditions | Yield |
---|---|
With overheated steam; sulfuric acid at 150℃; under 160 Torr; |
hydrogenchloride
2,6-dibromo-5-methoxy-4-methyl-4-nitro-cyclohex-2-enone
acetic acid
2-bromo-p-cresol
hydrogenchloride
5-ethoxy-2,6-dibromo-4-methyl-4-nitro-cyclohex-2-enone
acetic acid
2-bromo-p-cresol
2,4,6-tribromo-4-methylcyclohexa-2,5-dienone
2-bromo-p-cresol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: trifluoromethanesulfonic acid / CH2Cl2 / 0 °C 2: 54percent HI / H2O / 3 h / Heating 3: 84 percent Chromat. / bromine, triflic acid / 0.33 h View Scheme | |
Multi-step reaction with 3 steps 1: trifluoromethanesulfonic acid / CH2Cl2 / 0 °C 2: 54percent HI / H2O / 3 h / Heating 3: 24 percent Chromat. / bromine, triflic acid / 0.33 h View Scheme | |
Multi-step reaction with 3 steps 1: trifluoromethanesulfonic acid / CH2Cl2 / 0 °C 2: 54percent HI / H2O / 3 h / Heating 3: 8 percent Chromat. / bromine, triflic acid / 0.33 h View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 4.6 percent / bromine, potassium bromide, pyridine / H2O; diethyl ether / 0.17 h / -5 °C 2: trifluoromethanesulfonic acid / CH2Cl2 / 0 °C 3: 54percent HI / H2O / 3 h / Heating 4: 84 percent Chromat. / bromine, triflic acid / 0.33 h View Scheme | |
Multi-step reaction with 4 steps 1: 4.6 percent / bromine, potassium bromide, pyridine / H2O; diethyl ether / 0.17 h / -5 °C 2: trifluoromethanesulfonic acid / CH2Cl2 / 0 °C 3: 54percent HI / H2O / 3 h / Heating 4: 24 percent Chromat. / bromine, triflic acid / 0.33 h View Scheme | |
Multi-step reaction with 4 steps 1: 4.6 percent / bromine, potassium bromide, pyridine / H2O; diethyl ether / 0.17 h / -5 °C 2: trifluoromethanesulfonic acid / CH2Cl2 / 0 °C 3: 54percent HI / H2O / 3 h / Heating 4: 8 percent Chromat. / bromine, triflic acid / 0.33 h View Scheme |
2,3,6-tribromo-4-methyl-phenol
2-bromo-p-cresol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 54percent HI / H2O / 3 h / Heating 2: 84 percent Chromat. / bromine, triflic acid / 0.33 h View Scheme | |
Multi-step reaction with 2 steps 1: 54percent HI / H2O / 3 h / Heating 2: 24 percent Chromat. / bromine, triflic acid / 0.33 h View Scheme | |
Multi-step reaction with 2 steps 1: 54percent HI / H2O / 3 h / Heating 2: 8 percent Chromat. / bromine, triflic acid / 0.33 h View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: phosphorus (V)-bromide / 100 °C 2: ethanolic KOH View Scheme |
2-bromo-4-methyl-1-(2-propen-1-yloxy)benzene
A
2-bromo-p-cresol
B
2-bromo-4-methyl-1-propoxybenzene
Conditions | Yield |
---|---|
With sodium tetrahydroborate; ruthenium(III) chloride monohydrate In N-Methylformamide; water at 0℃; for 1h; |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 20h; Heating; | 100% |
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide | 91% |
With potassium carbonate In acetone for 4h; Reflux; | 90% |
2-bromo-p-cresol
ortho-nitrofluorobenzene
2-bromo-4-methyl-1-(2-nitrophenoxy)benzene
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 95℃; for 24h; Inert atmosphere; | 100% |
With potassium carbonate In dimethyl sulfoxide at 95℃; for 21h; | 95% |
2-bromo-p-cresol
allyl bromide
2-bromo-4-methyl-1-(2-propen-1-yloxy)benzene
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 20℃; | 99% |
With potassium carbonate In acetone | |
With potassium carbonate In acetone at 66℃; for 12h; | |
With potassium carbonate Inert atmosphere; | |
With potassium carbonate |
2-bromo-p-cresol
(4S) 3,4-dibenzyl[1,2,3]oxathiazolidine-2,2-dioxide
Conditions | Yield |
---|---|
Stage #1: 2-bromo-p-cresol; (4S) 3,4-dibenzyl[1,2,3]oxathiazolidine-2,2-dioxide With sodium hydride In N,N-dimethyl-formamide at 20℃; for 22h; Stage #2: With hydrogenchloride In N,N-dimethyl-formamide at 20℃; for 3h; Further stages.; | 99% |
bromoacetic acid tert-butyl ester
2-bromo-p-cresol
tert-butyl (2-bromo-4-methylphenoxy)acetate
Conditions | Yield |
---|---|
Stage #1: 2-bromo-p-cresol With potassium carbonate In acetone for 0.166667h; Stage #2: bromoacetic acid tert-butyl ester In acetone at 65℃; for 18h; | 99% |
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 12h; | |
Stage #1: 2-bromo-p-cresol With potassium carbonate In acetone for 0.166667h; Stage #2: bromoacetic acid tert-butyl ester In acetone at 65℃; for 18h; |
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid In dichloromethane at -78℃; for 4h; | 99% |
2-bromo-p-cresol
propargyl bromide
2-bromo-4-methyl-1-(prop-2-yn-1-yloxy)benzene
Conditions | Yield |
---|---|
With potassium carbonate In toluene; acetonitrile at 60℃; for 16h; | 99% |
With potassium carbonate In acetone at 80℃; for 5h; | 74% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | |
With potassium carbonate; sodium iodide In acetone for 6h; Reflux; | |
With potassium carbonate In acetone for 24h; Reflux; Inert atmosphere; |
2-bromo-p-cresol
(S)-tert-butyl 4-benzyl 1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide
C21H26BrNO3
Conditions | Yield |
---|---|
Stage #1: 2-bromo-p-cresol; (S)-tert-butyl 4-benzyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide With sodium hydride In N,N-dimethyl-formamide Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide | 99% |
2-bromo-p-cresol
2-mesitylmagnesium bromide
2',4',5,6'-tetramethyl-[1,1'-biphenyl]-2-ol
Conditions | Yield |
---|---|
Stage #1: 2-bromo-p-cresol With sodium hydride In tetrahydrofuran at 0 - 22℃; for 0.166667h; Kumada Cross-Coupling; Reflux; Stage #2: 2-mesitylmagnesium bromide With palladium(II) acetylacetonate for 12h; Reflux; | 99% |
2-bromo-p-cresol
2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
5-methyl[1,1':4',1''-terphenyl]-2-ol
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; palladium diacetate; sodium carbonate In water at 20 - 150℃; for 0.166667h; Suzuki Coupling; Sealed tube; Microwave irradiation; | 99% |
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 0.5h; Mitsunobu Displacement; Inert atmosphere; | 99% |
2-bromo-p-cresol
2-bromo-4-methyl-6-iodophenol
Conditions | Yield |
---|---|
With iodine; silver sulfate In ethanol at 20℃; | 98% |
With ammonia; iodine; potassium iodide In methanol; water at 60℃; | 96% |
With N-iodomorpholine-hydrogen iodide; potassium carbonate In water at 20℃; for 3h; Inert atmosphere; | 94.9% |
With ammonium hydroxide; iodine; potassium iodide | |
With iodine; silver sulfate In ethanol at 20℃; |
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 50℃; for 12h; Methylation; | 98% |
With potassium carbonate In N,N-dimethyl-formamide for 18h; | 94% |
With potassium carbonate | 84% |
With potassium carbonate In N,N-dimethyl-formamide for 24h; Reflux; |
2,2-dioxo-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester
2-bromo-p-cresol
C14H20BrNO3
Conditions | Yield |
---|---|
Stage #1: 2,2-dioxo-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester; 2-bromo-p-cresol With sodium hydride In N,N-dimethyl-formamide Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide | 98% |
2-bromo-p-cresol
(4R)-1,2,3-oxathiazolidine-3-carboxylic acid, 4-phenyl 1,1-dimethylethyl ester-2,2-dioxide
C20H24BrNO3
Conditions | Yield |
---|---|
Stage #1: 2-bromo-p-cresol; (4R)-1,2,3-oxathiazolidine-3-carboxylic acid, 4-phenyl 1,1-dimethylethyl ester-2,2-dioxide With sodium hydride In N,N-dimethyl-formamide Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide | 98% |
Conditions | Yield |
---|---|
With Methyl formate; copper(l) chloride In methanol at 110℃; for 2h; Autoclave; | 98% |
In methanol at 200℃; under 120012 Torr; for 0.0333333h; Temperature; Pressure; Time; Autoclave; | 13.38 g |
Conditions | Yield |
---|---|
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide at 0 - 20℃; for 38h; | 98% |
2-bromo-p-cresol
chloromethyl methyl ether
2-bromo-1-(methoxymethoxy)-4-methylbenzene
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane for 5h; Ambient temperature; | 97% |
With potassium carbonate In acetone at 20℃; | 93% |
With potassium carbonate In acetone at 40℃; for 1h; | 90% |
2-bromo-p-cresol
2-deuterio-4-methylphenol
Conditions | Yield |
---|---|
Stage #1: 2-bromo-p-cresol With n-butyllithium In diethyl ether; hexane at -78 - 20℃; for 3h; Inert atmosphere; Stage #2: With water-d2 In diethyl ether; hexane at 20℃; for 4h; | 97% |
Stage #1: 2-bromo-p-cresol With n-butyllithium In diethyl ether; hexane at 0 - 20℃; for 1.08333h; Inert atmosphere; Stage #2: With water-d2 In diethyl ether; hexane at 0℃; for 1h; Inert atmosphere; | 72% |
Stage #1: 2-bromo-p-cresol With n-butyllithium In tetrahydrofuran; toluene at 10℃; for 4h; Inert atmosphere; Stage #2: With water-d2 In tetrahydrofuran; toluene Inert atmosphere; |
2-bromo-p-cresol
(S)-4-Methyl-2,2-dioxo-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester
C15H22BrNO3
Conditions | Yield |
---|---|
Stage #1: 2-bromo-p-cresol; (S)-4-Methyl-2,2-dioxo-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester With sodium hydride In N,N-dimethyl-formamide Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide | 97% |
benzo[b]thiophene-2-boronic acid
2-bromo-p-cresol
Conditions | Yield |
---|---|
With bis(tri-t-butylphosphine)palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere; | 97% |
2-bromo-p-cresol
4-bromo-6-methyl-2H-pyran-2-one
4-(2-bromo-4-methylphenoxy)-6-methyl-2-pyrone
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 60℃; for 16h; | 96.1% |
2-bromo-p-cresol
(2s)-(+)-glycidyl 3-nitrobenzenesulfonate
(2S)-2-[(2-bromo-4-methylphenoxy)methyl]oxirane
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
With p-nitrobenzenesulfonic acid; cis-dichlorobis(triphenylphosphine)molybdenum; 1-ethyl-3-methylimidazolium tetrafluoroborate; bis-[(trifluoroacetoxy)iodo]benzene; 4,4'-di-tert-butyl-2,2'-bipyridine In N,N-dimethyl-formamide at 90℃; for 10h; Reagent/catalyst; Inert atmosphere; | 95.4% |
Conditions | Yield |
---|---|
Stage #1: 2-bromo-p-cresol With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 1h; Inert atmosphere; Stage #2: 2-bromoethanol In N,N-dimethyl-formamide at 120℃; Inert atmosphere; | 95% |
Stage #1: 2-bromo-p-cresol With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 1h; Stage #2: 2-bromoethanol In N,N-dimethyl-formamide at 60 - 120℃; for 12h; | 89% |
Conditions | Yield |
---|---|
With silver(l) oxide In water for 0.5h; Cooling with ice; | 95% |
With silver(l) oxide In water at 0℃; for 0.5h; Sealed tube; | 95% |
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