6627-55-0

Basic information

• Product Name: 2-Bromo-4-methylphenol
• Synonyms: 3-BROMO-4-HYDROXY-BENZYLIC ALCOHOL;AKOS BBB/368;2-BROMO-P-CRESOL;2-BROMO-4-METHYLPHENOL;2-bromo-p-creso;3-Bromo-4-hydroxytoluene;p-Cresol, 2-bromo-;2-Bromo-p-methylphenol
• CAS NO: 6627-55-0
• Molecular Formula: C₇H₇BrO
• Molecular Weight: 187.03
• EINECS: 229-595-7
• Product Categories: Aromatic Phenols;Phenol&Thiophenol&Mercaptan
• Mol File: 6627-55-0.mol
• Article Data: 85

Chemical Properties

• Melting Point: 213-214 °C
• Boiling Point: 213-214 °C(lit.)
• Flash Point: >230 °F
• Appearance: clear colourless to pale yellow liquid
• Density: 1.547 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.112mmHg at 25°C
• Refractive Index: n20/D 1.578(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 8.73±0.18(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 2-Bromo-4-methylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-4-methylphenol(6627-55-0)
• EPA Substance Registry System: 2-Bromo-4-methylphenol(6627-55-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-21/22
• Safety Statements: 26-37/39-36/37/39-24/25
• WGK Germany: 3
• RTECS: GO6868200
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 6627-55-0(Hazardous Substances Data)

Usage

Chemical Properties

clear colourless to pale yellow liquid

Uses

It is applied as a compound responsible for iodine off-flavor in wines.

InChI:InChI=1/C7H7BrO/c1-5-2-3-7(9)6(8)4-5/h2-4,9H,1H3

Synthetic route

p-cresol (106-44-5) → 2-bromo-p-cresol (6627-55-0)

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 (22002-45-5) → 2-bromo-p-cresol (6627-55-0)

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 (25458-49-5) → 2-bromo-p-cresol (6627-55-0)

Conditions	Yield
With tris(2,2'-bipyridyl)ruthenium dichloride; carbon tetrabromide In acetonitrile at 20℃; Irradiation;	97%

p-cresol (106-44-5) → 2-bromo-p-cresol (6627-55-0) + 3,5-dibromo-4-hydroxytoluene (2432-14-6)

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%

p-cresol (106-44-5) → 2-bromo-p-cresol (6627-55-0) + 3-bromo-p-cresol (60710-39-6)

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%

meta-bromotoluene (591-17-3) → 2-bromo-p-cresol (6627-55-0) + 4-Bromo-2-methylphenol (2362-12-1)

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 (17902-32-8) → 2-bromo-p-cresol (6627-55-0)

Conditions	Yield
With tris(2,2'-bipyridyl)ruthenium dichloride; carbon tetrabromide In acetonitrile at 20℃; Irradiation;	69%

1-methylcyclohexan-4-one (589-92-4) → 2-bromo-p-cresol (6627-55-0)

Conditions	Yield
With diethyl dibromomalonate at 100℃; for 48h; Bromination; aromatization;	51%

2-bromo-p-toluidine (583-68-6) → 2-bromo-p-cresol (6627-55-0)

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 (65849-33-4) → 2-bromo-p-cresol (6627-55-0)

Conditions	Yield
With potassium hydroxide

sodium 4-methylphenoxide (1121-70-6) → 2-bromo-p-cresol (6627-55-0) + 3,5-dibromo-4-hydroxytoluene (2432-14-6)

Conditions	Yield
With carbon disulfide; bromine

p-cresol (106-44-5) → 2-bromo-p-cresol (6627-55-0) + 3,5-dibromo-4-hydroxytoluene (2432-14-6) + 3-bromo-p-cresol (60710-39-6) + 2,5-dibromo-p-cresol (344249-21-4)

Conditions	Yield
With trifluorormethanesulfonic acid; bromine for 0.333333h;	A 84 % Chromat. B 3 % Chromat. C 1 % Chromat. D 1 % Chromat.

p-cresol (106-44-5) → 2-bromo-p-cresol (6627-55-0) + 3,5-dibromo-4-hydroxytoluene (2432-14-6) + 3-bromo-p-cresol (60710-39-6) + 2,5-dibromo-p-cresol (344249-21-4) + 2,3-dibromo-4-methylphenol

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 (106-44-5) → 2-bromo-p-cresol (6627-55-0) + 3,5-dibromo-4-hydroxytoluene (2432-14-6) + 3-bromo-p-cresol (60710-39-6) + 2,3-dibromo-4-methylphenol

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 (106-44-5) → 2-bromo-p-cresol (6627-55-0) + 3-bromo-p-cresol (60710-39-6) + 2,5-dibromo-p-cresol (344249-21-4) + 2,3-dibromo-4-methylphenol

Conditions	Yield
With trifluorormethanesulfonic acid; bromine for 0.333333h; Further byproducts given;	A 8 % Chromat. B 61 % Chromat. C 15 % Chromat. D 2 % Chromat.

3-bromo-p-cresol (60710-39-6) → p-cresol (106-44-5) + 2-bromo-p-cresol (6627-55-0)

Conditions	Yield
With trifluorormethanesulfonic acid Product distribution;

p-cresol (106-44-5) + chloroform (67-66-3) + bromine (7726-95-6) → 2-bromo-p-cresol (6627-55-0)

p-cresol (106-44-5) + bromine (7726-95-6) + natrium carbonate → 2-bromo-p-cresol (6627-55-0)

3.5-dibromo-1-nitro-2-methoxy-1-methyl-cyclohexen-(2)-one-(4) → 2-bromo-p-cresol (6627-55-0)

Conditions	Yield
With hydrogenchloride; acetic acid; zinc

5-bromo-4-hydroxy-toluene-sulfonic acid-(3) → 2-bromo-p-cresol (6627-55-0)

Conditions	Yield
With overheated steam; sulfuric acid at 150℃; under 160 Torr;

hydrogenchloride (7647-01-0) + 2,6-dibromo-5-methoxy-4-methyl-4-nitro-cyclohex-2-enone (859818-05-6) + acetic acid (64-19-7) + zinc → 2-bromo-p-cresol (6627-55-0)

hydrogenchloride (7647-01-0) + 5-ethoxy-2,6-dibromo-4-methyl-4-nitro-cyclohex-2-enone (859179-90-1) + acetic acid (64-19-7) + zinc → 2-bromo-p-cresol (6627-55-0)

2,4,6-tribromo-4-methylcyclohexa-2,5-dienone (39953-10-1) → 2-bromo-p-cresol (6627-55-0)

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

3,5-dibromo-4-hydroxytoluene (2432-14-6) → 2-bromo-p-cresol (6627-55-0)

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 (36776-51-9) → 2-bromo-p-cresol (6627-55-0)

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

p-cresyl benzoate (614-34-6) → 2-bromo-p-cresol (6627-55-0)

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 (2120-18-5) → 2-bromo-p-cresol (6627-55-0) + 2-bromo-4-methyl-1-propoxybenzene (99187-38-9)

Conditions	Yield
With sodium tetrahydroborate; ruthenium(III) chloride monohydrate In N-Methylformamide; water at 0℃; for 1h;

2-bromo-p-cresol (6627-55-0) + benzyl bromide (100-39-0) → 1-(benzyloxy)-2-bromo-4-methylbenzene (2830-53-7)

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 (6627-55-0) + ortho-nitrofluorobenzene (1493-27-2) → 2-bromo-4-methyl-1-(2-nitrophenoxy)benzene (856382-90-6)

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 (6627-55-0) + allyl bromide (106-95-6) → 2-bromo-4-methyl-1-(2-propen-1-yloxy)benzene (2120-18-5)

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 (6627-55-0) + (4S) 3,4-dibenzyl[1,2,3]oxathiazolidine-2,2-dioxide (511286-63-8) → benzyl [(S)-1-benzyl-2-(2-bromo-4-methylphenoxy)ethyl]amine

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 (5292-43-3) + 2-bromo-p-cresol (6627-55-0) → tert-butyl (2-bromo-4-methylphenoxy)acetate (1240286-85-4)

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;

2-bromo-p-cresol (6627-55-0) + isobutene (115-11-7) → 1-tert-butoxy-2-bromo-4-methylbenzene (960309-86-8)

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane at -78℃; for 4h;	99%

2-bromo-p-cresol (6627-55-0) + propargyl bromide (106-96-7) → 2-bromo-4-methyl-1-(prop-2-yn-1-yloxy)benzene (1020991-05-2)

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 (6627-55-0) + (S)-tert-butyl 4-benzyl 1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide (1105712-07-9) → C21H26BrNO3 (1441005-72-6)

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 (6627-55-0) + 2-mesitylmagnesium bromide (2633-66-1) → 2',4',5,6'-tetramethyl-[1,1'-biphenyl]-2-ol (1448442-52-1)

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 (6627-55-0) + 2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (144432-80-4) → 5-methyl[1,1':4',1''-terphenyl]-2-ol (1310321-62-0)

Conditions	Yield
With tetrabutylammomium bromide; palladium diacetate; sodium carbonate In water at 20 - 150℃; for 0.166667h; Suzuki Coupling; Sealed tube; Microwave irradiation;	99%

methyl propargyl alcohol (764-01-2) + 2-bromo-p-cresol (6627-55-0) → 2-bromo-1-(but-2-yn-1-yloxy)-4-methylbenzene

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 0.5h; Mitsunobu Displacement; Inert atmosphere;	99%

2-bromo-p-cresol (6627-55-0) → 2-bromo-4-methyl-6-iodophenol (180639-95-6)

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℃;

2-bromo-p-cresol (6627-55-0) + methyl iodide (74-88-4) → 2-bromo-4-methylanisole (22002-45-5)

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 (459817-82-4) + 2-bromo-p-cresol (6627-55-0) → C14H20BrNO3 (1441005-46-4)

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 (6627-55-0) + (4R)-1,2,3-oxathiazolidine-3-carboxylic acid, 4-phenyl 1,1-dimethylethyl ester-2,2-dioxide (1209467-60-6) → C20H24BrNO3 (1441005-63-5)

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%

2-bromo-p-cresol (6627-55-0) + sodium methylate (124-41-4) → 2-Methoxy-4-methylphenol (93-51-6)

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

1,3,5-trichloro-2,4,6-triazine (108-77-0) + 2-bromo-p-cresol (6627-55-0) → 2-(2-bromo-4-methylphenoxy)-4,6-dichloro-1,3,5-triazine

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide at 0 - 20℃; for 38h;	98%

2-bromo-p-cresol (6627-55-0) + chloromethyl methyl ether (107-30-2) → 2-bromo-1-(methoxymethoxy)-4-methylbenzene (104750-60-9)

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 (6627-55-0) → 2-deuterio-4-methylphenol (115943-93-6)

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 (6627-55-0) + (S)-4-Methyl-2,2-dioxo-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester (439948-91-1) → C15H22BrNO3 (1441005-57-7)

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 (98437-23-1) + 2-bromo-p-cresol (6627-55-0) → 2-(benzo[b]thiophen-2-yl)-4-methylphenol

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 (6627-55-0) + 4-bromo-6-methyl-2H-pyran-2-one (132559-91-2) → 4-(2-bromo-4-methylphenoxy)-6-methyl-2-pyrone (1259312-84-9)

Conditions	Yield
With potassium carbonate In acetone at 60℃; for 16h;	96.1%

2-bromo-p-cresol (6627-55-0) + (2s)-(+)-glycidyl 3-nitrobenzenesulfonate (115314-14-2) → (2S)-2-[(2-bromo-4-methylphenoxy)methyl]oxirane (1351163-91-1)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	96%

2-bromo-p-cresol (6627-55-0) + o-nitrobenzonitrile (612-24-8) → 5-methyl-2-(2-nitrophenyl)-1,3-benzothiazole

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%

2-bromo-p-cresol (6627-55-0) + 2-bromoethanol (540-51-2) → 2-(2-bromo-4-methylphenoxy)ethan-1-ol

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%

2-bromo-p-cresol (6627-55-0) + diethylazodicarboxylate (1972-28-7) → 1-(3-bromo-1-methyl-4-oxocyclohexa-2,5-dien-1-yl)hydrazine-1,2-dicarboxylic acid diethyl ester

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%

Upstream product

• 589-92-4 1-methylcyclohexan-4-one 
• 591-17-3 meta-bromotoluene 
• 25458-49-5 1-(methoxymethoxy)-4-methylbenzene 
• 17902-32-8 trimethyl(4-methylphenoxy)silane 
• 2120-18-5 2-bromo-4-methyl-1-(2-propen-1-yloxy)benzene 
• 22002-45-5 2-bromo-4-methylanisole 
• 614-34-6 p-cresyl benzoate 
• 36776-51-9 2,3,6-tribromo-4-methyl-phenol 
• 2432-14-6 3,5-dibromo-4-hydroxytoluene 
• 39953-10-1 2,4,6-tribromo-4-methylcyclohexa-2,5-dienone 
• 7647-01-0 hydrogenchloride 
• 859179-90-1 5-ethoxy-2,6-dibromo-4-methyl-4-nitro-cyclohex-2-enone 
• 64-19-7 acetic acid 
• 859818-05-6 2,6-dibromo-5-methoxy-4-methyl-4-nitro-cyclohex-2-enone 

Downstream Products

• 99187-38-9 2-bromo-4-methyl-1-propoxybenzene 
• 76429-63-5 2-bromo-1-(2-bromoethoxy)-4-methylbenzene 
• 22002-45-5 2-bromo-4-methylanisole 
• 76429-82-8 1-Bromo-5-(2-bromo-4-methylphenoxy)pentane 
• 2120-18-5 2-bromo-4-methyl-1-(2-propen-1-yloxy)benzene 
• 36776-51-9 2,3,6-tribromo-4-methyl-phenol 
• 344249-21-4 2,5-dibromo-p-cresol 
• 13979-81-2 3,5-dibromo-4-methylphenol 
• 87682-04-0 3,3'-Dibromo-5,5'-dimethyl<1,1'-biphenyl>-2,2'-diol 
• 30435-75-7 2-bromo-4-methyl-6-nitroanisole 
• 112251-92-0 (Z)-4-bromo-3-methoxy-6-methyl-6-nitrocyclohexa-2,4-dienyl acetate 
• 854663-23-3 bis-(3-bromo-2-hydroxy-5-methyl-benzyl)-ether 

Relevant articles and documents

Electrophotocatalytic C?H Heterofunctionalization of Arenes

The electrophotocatalytic heterofunctionalization of arenes is described. Using 2,3-dichloro-5,6-dicyanoquinone (DDQ) under a mild electrochemical potential with visible-light irradiation, arenes undergo oxidant-free hydroxylation, alkoxylation, and amination with high chemoselectivity. In addition to batch reactions, an electrophotocatalytic recirculating flow process is demonstrated, enabling the conversion of benzene to phenol on a gram scale.

A convenient and efficient H2SO4-promoted regioselective monobromination of phenol derivatives using N-bromosuccinimide

A convenient, rapid H2SO4-promoted regioselective monobromination reaction with N-bromosuccinimide was developed. The desired para-monobrominated or ortho-monobrominated products of phenol derivatives were obtained in good to excellent yields with high selectivity. Regioselective chlorination and iodination were also achieved in the presence of H2SO4 using N-chlorosuccinimide and N-iodosuccinimide, respectively.

A phenol compound high regioselective bromination method

The invention discloses a phenol compound high regioselective bromination of the method, the method to trimethyl silane as brominating agent, in order to aryl sulfoxide as activator, with the phenol compound in the 0 - 50 °C lower, in a solvent, the reaction is stirred under an atmosphere of nitrogen at 1 - 12 hours, to realize the phenol compound high regioselective bromination, filtered, extraction columns chromatography separation to obtain the bromo phenol compound. This invention adopts the aryl sulfoxide as activator, sulfoxide substituted Kiev, on the one hand so that the phenol compound bromo the higher selectivity of the reaction region, and when the phenol compound hydroxy alignment not substituted basetime, regional selective para - bromo product, when the phenol compound hydroxy position there is substituted basetime, selective ortho - bromo product obtained; on the other hand if it through the filter, the extraction can be realized at the same time the isolation and purification of the recycling of the by-product, compared with column chromatography, reduces the separation and purification cost.