7697-28-1

Basic information

• Product Name: 4-Bromo-3-methylbenzoic acid
• Synonyms: 4-BROMO-M-TOLUIC ACID;4-BROMO-3-METHYLBENZOIC ACID;3-methyl-4-bromobenzoic acid;RARECHEM AL BO 1293;4-Bromo-3-methyl;4-Bromo-3-methylbenz;2-Bromo-5-carboxytoluene, 4-Bromo-m-toluic acid;3 - Methyl - 4 - broMine benzoic acid
• CAS NO: 7697-28-1
• Molecular Formula: C₈H₇BrO₂
• Molecular Weight: 215.04
• EINECS: 231-713-7
• Product Categories: blocks;Bromides;Carboxes;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic acid;Organic acids;Acids & Esters;Bromine Compounds;C8;Carbonyl Compounds;Carboxylic Acids
• Mol File: 7697-28-1.mol
• Article Data: 8

Chemical Properties

• Melting Point: 212-216 °C(lit.)
• Boiling Point: 311.4 °C at 760 mmHg
• Flash Point: 142.1 °C
• Appearance: Yellow to orange to tan/Powder
• Density: 1.599 g/cm₃
• Vapor Pressure: 0.000243mmHg at 25°C
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.04±0.10(Predicted)
• BRN: 2356649
• CAS DataBase Reference: 4-Bromo-3-methylbenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-3-methylbenzoic acid(7697-28-1)
• EPA Substance Registry System: 4-Bromo-3-methylbenzoic acid(7697-28-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 7697-28-1(Hazardous Substances Data)

Usage

General Description

4-Bromo-3-methylbenzoic acid is a chemical compound with the formula C8H7BrO2. It is a white crystalline solid that is used in the synthesis of various pharmaceuticals and organic compounds. 4-Bromo-3-methylbenzoic acid has a bromo group and a methyl group attached to a benzoic acid molecule. It is used in the production of drugs and is also used as a reagent in organic synthesis. 4-Bromo-3-methylbenzoic acid is also known for its ability to undergo various chemical reactions and is used in the pharmaceutical and chemical industries for the production of various compounds.

InChI:InChI=1/C8H7BrO2/c1-5-4-6(8(10)11)2-3-7(5)9/h2-4H,1H3,(H,10,11)/p-1

Synthetic route

4-amino 3-methylbenzoic acid (2486-70-6) → 4-bromo-3-methylbenzoic acid (7697-28-1)

Conditions	Yield
Stage #1: 4-amino 3-methylbenzoic acid With hydrogen bromide In water at 25℃; for 1h; Stage #2: With sodium nitrate In water at -2 - -1℃; for 1.75h; Stage #3: With hydrogen bromide; copper(I) bromide In water at -2 - 70℃; for 2h;	90%
Diazotization.Kochen der Diazoverbindung mit Bromwasserstoffsaeure;
With hydrogen bromide; sodium nitrite; copper(I) chloride In water

4,4'-dibromo-5,3'-dimethyl-2-nitrodiphenylmethane (84797-77-3) → 4-bromo-3-methylbenzoic acid (7697-28-1) + 6-bromo-5-methyl-3-(4'-bromo-3'-methylphenyl)-2,1-isoxazole (93099-47-9) + 3,6-dibromo-2,7-dimethylacridone (84658-94-6)

Conditions	Yield
With sulfuric acid In ethanol for 5h; Irradiation;	A 63% B 20% C 6%
With sulfuric acid In ethanol for 5h; Product distribution; Mechanism; Irradiation;	A 51% B 20% C 6%

4-bromo-3-methyl-N-(2-methyl-4-cyanophenyl)benzamide (146308-26-1) → 4-bromo-3-methylbenzoic acid (7697-28-1) + 4-amino-3-methylbenzonitrile (78881-21-7)

Conditions	Yield
With potassium hydroxide In ethanol a) 70 deg C, 4.5 h, b) 80 deg C, 3 h; Yields of byproduct given;	A 63% B n/a
With potassium hydroxide In ethanol a) 70 deg C, 4.5 h, b) 80 deg C, 3 h; Yield given;	A 63% B n/a

1-bromo-2,4-dimethylbenzene (583-70-0) → 4-bromo-3-methylbenzoic acid (7697-28-1)

Conditions	Yield
With nitric acid	60%
With nitric acid for 24h; Heating / reflux;	60%
With nitric acid at 150℃;
With nitric acid

n-butyllithium (109-72-8, 29786-93-4) + 1,4-dibromo-2-methylbenzene (615-59-8) → 4-bromo-3-methylbenzoic acid (7697-28-1)

Conditions	Yield
With diethyl ether Aufgiessen des Reaktionsgemisches auf festes Kohlendioxid;

1,4-dibromo-2-methylbenzene (615-59-8) → 2-methylterephthalic acid (5156-01-4) + 4-bromo-3-methylbenzoic acid (7697-28-1)

Conditions	Yield
With n-butyllithium; Petroleum ether anschliessendes Behandeln mit festem Kohlendioxid;

1-bromo-4-isopropyl-2-methyl-benzene (92243-75-9) → 4-bromo-3-methylbenzoic acid (7697-28-1)

Conditions	Yield
With nitric acid

1-(4-bromo-3-methylphenyl)ethan-1-one (37074-40-1) → 4-bromo-isophthalic acid (6939-93-1) + 4-bromo-3-methylbenzoic acid (7697-28-1)

Conditions	Yield
With potassium permanganate
With alkaline potassium permanganate

m-Toluic acid (99-04-7) → 4-bromo-3-methylbenzoic acid (7697-28-1) + 2-bromo-5-methylbenzoic acid (6967-82-4)

Conditions	Yield
With bromine

amino-5-bromo-2-toluene (6933-10-4) + copper(I) cyanide (544-92-3) → 4-bromo-3-methylbenzoic acid (7697-28-1)

Conditions	Yield
(i) NaNO2, aq. HCl, (ii) /BRN= 3587244/, (iii) NaOH, EtOH; Multistep reaction;

bromine (7726-95-6) + m-Toluic acid (99-04-7) → 4-bromo-3-methylbenzoic acid (7697-28-1) + 2-bromo-5-methylbenzoic acid (6967-82-4)

n-butyllithium (109-72-8, 29786-93-4) + 1,4-dibromo-2-methylbenzene (615-59-8) + petroleum ether → 4-bromo-2-methylbenzoic acid (68837-59-2) + 4-bromo-3-methylbenzoic acid (7697-28-1)

Conditions	Yield
at 20℃; anschliessend Behandlung mit CO2;

1-bromo-2,4-dimethylbenzene (583-70-0) + chromic acid mixture → 4-bromo-3-methylbenzoic acid (7697-28-1)

4-ethyl-1-bromo-2-methyl-benzene (90560-90-0) + nitric acid (7697-37-2) → 4-bromo-3-methylbenzoic acid (7697-28-1)

1-bromo-4-isopropyl-2-methyl-benzene (92243-75-9) + nitric acid (7697-37-2) → 4-bromo-3-methylbenzoic acid (7697-28-1)

asymm. bromo-m-xylene → 4-bromo-3-methylbenzoic acid (7697-28-1)

Conditions	Yield
With dichromate mixture

1-(4-bromo-3-methylphenyl)ethan-1-one (37074-40-1) + KMnO4 + aqueous KOH → 4-bromo-3-methylbenzoic acid (7697-28-1)

4-Bromobenzoic acid (586-76-5) + methyl iodide (74-88-4) → 4-bromo-3-methylbenzoic acid (7697-28-1)

Conditions	Yield
Stage #1: 4-Bromobenzoic acid With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran; hexane at -78℃; for 4h; Stage #2: methyl iodide In tetrahydrofuran; hexane at -78 - 20℃;	12 % Spectr.

3-Methylacetanilide (537-92-8) → 4-bromo-3-methylbenzoic acid (7697-28-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) (bromination), (ii) (hydrolysis) 2: (i) NaNO2, aq. HCl, (ii) /BRN= 3587244/, (iii) NaOH, EtOH View Scheme

4-Bromo-3-methylbenzoic acid methyl ester (148547-19-7) → 4-bromo-3-methylbenzoic acid (7697-28-1)

Conditions	Yield
Stage #1: 4-Bromo-3-methylbenzoic acid methyl ester With water; sodium hydroxide In tetrahydrofuran at 20℃; for 16h; Stage #2: With hydrogenchloride In water

4-bromo-3-methylbenzoic acid (7697-28-1) → 4-bromo-3-methylbenzylalcohol (149104-89-2)

Conditions	Yield
With borane-THF In tetrahydrofuran at 0 - 20℃;	100%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 0.25h;	100%
With borane In tetrahydrofuran at -30 - 20℃;	98%

4-bromo-3-methylbenzoic acid (7697-28-1) + phenylboronic acid (98-80-6) → 2-methyl[1,1'-biphenyl]-4-carboxylic acid (178313-67-2)

Conditions	Yield
With disodium hydrogenphosphate; disodium bis(2-aminopyrimidine-4,6-diolate)palladium acetate In water at 50 - 120℃; for 0.166667h; Microwave irradiation;	100%
With disodium hydrogenphosphate; Pd(OAc)2(2-amino-4,6-dihydroxypyrimidine disodium salt)2 In water at 120℃; for 0.166667h; Suzuki-Miyaura coupling; Microwave irradiation;	99%
With potassium fluoride; palladium diacetate; XPhos In tetrahydrofuran for 1h; Heating / reflux;

3-METHOXYBENZYLAMINE (5071-96-5) + 4-bromo-3-methylbenzoic acid (7697-28-1) → 4-bromo-N-(3-methoxybenzyl)-3-methylbenzamide (1623120-19-3)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20℃; for 1h; Inert atmosphere;	100%

4-bromo-3-methylbenzoic acid (7697-28-1) + m-tolylboronic acid (17933-03-8) → 3-methyl-4-(m-tolyl)benzoic acid

Conditions	Yield
With disodium hydrogenphosphate; disodium bis(2-aminopyrimidine-4,6-diolate)palladium acetate In water at 50 - 120℃; for 0.166667h; Microwave irradiation;	100%

4-bromo-3-methylbenzoic acid (7697-28-1) + isopropylamine (75-31-0) → 4-bromo-N-isopropyl-3-methylbenzamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate at 0 - 20℃; for 1h;	100%

4-bromo-3-methylbenzoic acid (7697-28-1) + 2-Methylphenylboronic acid (16419-60-6) → 2,2’-dimethyl-1,1’-biphenyl-4-carboxylic acid (69535-85-9)

Conditions	Yield
With disodium hydrogenphosphate; Pd(OAc)2(2-amino-4,6-dihydroxypyrimidine disodium salt)2 In water at 120℃; for 0.166667h; Suzuki-Miyaura coupling; Microwave irradiation;	99%
With disodium hydrogenphosphate; disodium bis(2-aminopyrimidine-4,6-diolate)palladium acetate In water at 50 - 120℃; for 0.166667h; Microwave irradiation;	95%

3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)aniline (1428155-06-9) + 4-bromo-3-methylbenzoic acid (7697-28-1) → 4-bromo-3-methyl-N-(3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)phenyl)benzamide (1428155-45-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;	99%

methanol (67-56-1) + 4-bromo-3-methylbenzoic acid (7697-28-1) → 4-Bromo-3-methylbenzoic acid methyl ester (148547-19-7)

Conditions	Yield
With sulfuric acid In methanol for 14h; Reflux;	97%
With sulfuric acid Reflux;	95%
Stage #1: methanol With acetyl chloride for 0.416667h; Stage #2: 4-bromo-3-methylbenzoic acid for 18h; Heating / reflux;	93%

ethanol (64-17-5) + 4-bromo-3-methylbenzoic acid (7697-28-1) → ethyl 3-methyl-4-bromobenzoate (160313-69-9)

Conditions	Yield
With thionyl chloride at 83℃; for 6h;	96%
With sulfuric acid In toluene for 1h; Heating;	80%
With hydrogenchloride

N-trimethylsilylmethylamine (18166-02-4) + 4-bromo-3-methylbenzoic acid (7697-28-1) → 4-bromo-3-methyl-N-trimethylsilanylmethyl-benzamide (1370257-42-3)

Conditions	Yield
Stage #1: 4-bromo-3-methylbenzoic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h; Stage #2: N-trimethylsilylmethylamine In dichloromethane at 20℃; Product distribution / selectivity;	94%

cyclobutylamine (2516-34-9) + 4-bromo-3-methylbenzoic acid (7697-28-1) → 4-bromo-N-cyclobutyl-3-methylbenzamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;	94%

4-bromo-3-methylbenzoic acid (7697-28-1) + methylamine (74-89-5) → 4-bromo-N,3-dimethylbenzamide

Conditions	Yield
Stage #1: 4-bromo-3-methylbenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h; Stage #2: methylamine In ethanol at 20℃; for 0.5h;	94%

2-(2-Hydroxyethyl)pyridine (103-74-2) + 4-bromo-3-methylbenzoic acid (7697-28-1) → 2-(2-pyridyl)ethyl 4-bromo-3-methylbenzoate (920270-48-0)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 16h; Inert atmosphere;	92%

4-bromo-3-methylbenzoic acid (7697-28-1) + 3-(8-nitroquinolin-4-yl)benzenamine → 4-bromo-3-methyl-N-(3-(8-nitroquinolin-4-yl)phenyl)benzamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃;	92%

4-bromo-3-methylbenzoic acid (7697-28-1) + 4-carboxyphenylboronic acid (14047-29-1) → 2-methyl-[1,1′-biphenyl]-4,4′-dicarboxylic acid (1186048-28-1)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; triphenylphosphine In water; N,N-dimethyl-formamide at 90℃; for 24h;	91%
With {1,1'-bis(diphenylphosphino)ferrocene} palladium dibromide; sodium carbonate In water; N,N-dimethyl-formamide at 90℃; for 3h; Inert atmosphere;
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 24h; Reflux;

4-bromo-3-methylbenzoic acid (7697-28-1) + 4-phenyl-2,3-dihydro-1H-indole (179473-53-1) → (4-bromo-3-methylphenyl)(4-phenylindolin-1-yl)methanone

Conditions	Yield
Stage #1: 4-bromo-3-methylbenzoic acid; 4-phenyl-2,3-dihydro-1H-indole With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; Stage #2: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h;	90.2%
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 3h;	87%

4-bromo-3-methylbenzoic acid (7697-28-1) + bis(pinacol)diborane (73183-34-3) → 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (269409-74-7)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 120℃; for 0.25h; Microwave irradiation;	90%
With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In N,N-dimethyl-formamide at 120℃; for 0.25h; Microwave irradiation;	90%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 125℃; for 0.333333h; Microwave irradiation;	74%
With triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane at 20 - 80℃;

di-tert-butyl dicarbonate (24424-99-5) + 4-bromo-3-methylbenzoic acid (7697-28-1) → tert-butyl 4-bromo-3-methylbenzoate (347174-28-1)

Conditions	Yield
With dmap In tetrahydrofuran Reflux;	87%
With dmap In tetrahydrofuran Reflux;	87%
With dmap In tetrahydrofuran; tert-butyl alcohol at 70℃; for 12h; Inert atmosphere;	70%

4-bromo-3-methylbenzoic acid (7697-28-1) → 1-bromo-2-methyl-4-(trifluoromethyl)benzene (929000-62-4)

Conditions	Yield
With sulfur tetrafluoride; hydrogen fluoride at 85℃; for 24h; Autoclave; Inert atmosphere;	87%

4-bromo-3-methylbenzoic acid (7697-28-1) + potassium tert-butylate (865-47-4) → tert-butyl 4-bromo-3-methylbenzoate (347174-28-1)

Conditions	Yield
Stage #1: 4-bromo-3-methylbenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2.33333h; Stage #2: potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 1h;	86%
Stage #1: 4-bromo-3-methylbenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 2h; Inert atmosphere; Stage #2: potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 2h;	69%
Stage #1: 4-bromo-3-methylbenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 4h; Inert atmosphere; Stage #2: potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere;	42%
Stage #1: 4-bromo-3-methylbenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h; Stage #2: potassium tert-butylate In tetrahydrofuran at 20℃; for 0.5h;

4-bromo-3-methylbenzoic acid (7697-28-1) → 4-bromo-3-(bromomethyl)benzoic acid (887757-31-5)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 72h; Concentration; Reflux;	86%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 76℃; for 72h;	86%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 48h; Reflux;	86%

4-bromo-3-methylbenzoic acid (7697-28-1) + 4-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)indoline → C24H20BrNO3

Conditions	Yield
Stage #1: 4-bromo-3-methylbenzoic acid; 4-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)indoline With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; Stage #2: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h;	85.5%

oxalyl dichloride (79-37-8) + 4-bromo-3-methylbenzoic acid (7697-28-1) → tert-butyl 4-bromo-3-methylbenzoate (347174-28-1)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran; N-methyl-acetamide; dichloromethane; water	85%

4-bromo-3-methylbenzoic acid (7697-28-1) + potassium phenyltrifluoborate → C14H11BrO2

Conditions	Yield
With dipotassium hydrogenphosphate; oxygen; palladium diacetate; p-benzoquinone In tert-butyl alcohol at 100℃; under 22801.5 Torr; for 24h; regioselective reaction;	85%

4-bromo-3-methylbenzoic acid (7697-28-1) + methyl iodide (74-88-4) → 4-Bromo-3-methylbenzoic acid methyl ester (148547-19-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 2.5h;	83.1%

4-bromo-3-methylbenzoic acid (7697-28-1) + dimethyl amine (124-40-3) → 4-bromo-N,N,3-trimethylbenzamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In tetrahydrofuran; dichloromethane at 20℃; for 16h;	83%
With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In ethanol; water at 20℃; for 24h;	65%

4-bromo-3-methylbenzoic acid (7697-28-1) + {2‐azabicyclo[2.1.1]hexan‐1‐yl}methanamine → N‐({2‐benzyl‐2‐azabicyclo[2.1.1]hexan‐1‐yl}methyl)‐4‐bromo‐3‐methylbenzamide

Conditions	Yield
Stage #1: 4-bromo-3-methylbenzoic acid With 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.5h; Stage #2: {2‐azabicyclo[2.1.1]hexan‐1‐yl}methanamine In dichloromethane at 20℃; for 1h;	82%

2-fluoro-N1-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)benzene-1,4-diamine (1428155-04-7) + 4-bromo-3-methylbenzoic acid (7697-28-1) → 4-bromo-N-(3-fluoro-4-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-ylamino)phenyl)-3-methylbenzamide (1428155-17-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;	80%

4-bromo-3-methylbenzoic acid (7697-28-1) + methyl 6-aminocaproate hydrochloride (1926-80-3) → methyl 6-(4-bromo-3-methylbenzamido)hexanoate (1255952-05-6)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trimethylamine In dichloromethane for 20h; Inert atmosphere;	78%

Upstream product

• 583-70-0 1-bromo-2,4-dimethylbenzene 
• 2486-70-6 4-amino 3-methylbenzoic acid 
• 37074-40-1 1-(4-bromo-3-methylphenyl)ethan-1-one 
• 99-04-7 m-Toluic acid 
• 7726-95-6 bromine 
• 148547-19-7 4-Bromo-3-methylbenzoic acid methyl ester 
• 537-92-8 3-Methylacetanilide 
• 586-76-5 4-Bromobenzoic acid 
• 74-88-4 methyl iodide 
• 92243-75-9 1-bromo-4-isopropyl-2-methyl-benzene 
• 7697-37-2 nitric acid 
• 90560-90-0 4-ethyl-1-bromo-2-methyl-benzene 
• 109-72-8 n-butyllithium 
• 615-59-8 1,4-dibromo-2-methylbenzene 

Downstream Products

• 160313-69-9 ethyl 3-methyl-4-bromobenzoate 
• 499-76-3 4-hydroxy-3-methylbenzoic acid 
• 99-04-7 m-Toluic acid 
• 21900-25-4 4-bromo-3-methylbenzoyl chloride 
• 149104-89-2 4-bromo-3-methylbenzylalcohol 
• 210228-01-6 1-(4-Bromo-3-methyl phenyl)-propan-1-one 
• 78775-11-8 3-methyl-4-bromobenzaldehyde 
• 347174-28-1 tert-butyl 4-bromo-3-methylbenzoate 
• 85588-37-0 3-methyl-4-bromo benzophenone 
• 85588-40-5 3-bromomethyl-4-bromobenzophenone 
• 85588-43-8 6-bromo-3-benzoylphenyl acetonitrile 
• 85588-46-1 2-(6-bromo-3-benzoylphenyl)propionitrile 
• 121-91-5 isophthalic acid 
• 149556-37-6 4-bromo-3-methyl benzoic acid N-cyclopentyl-N-cyclohexyl amide 

Relevant articles and documents

ORGANIC COMPOUNDS

The present invention provides compounds of the following structure; [in-line-formulae]A-L1-B-C-D[/in-line-formulae] that are useful for treating or preventing conditions or disorders associated with DGAT1 activity in animals, particularly humans.

2,3,4,5-TETRAHYDRO-1H-1,5-BENZODIAZEPINE DERIVATIVE AND MEDICINAL COMPOSITION

A 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine derivative represented by the generalformula (1): [Chemical formula 1] (1) or a pharmaceutically acceptable saltthereof. They are useful as a therapeutic/preventive agent for diabetes, diabeticnephropathy, or glomerulosclerosis.

The first regioselective metalation and functionalization of unprotected 4-halobenzoic acids

(Chemical Equation Presented) By treatment with s-BuLi, s-BuLi/TMEDA, or t-BuLi at ～-78°C, 4-fluoro- and 4-chlorobenzoic acids (1a,b) are metalated preferentially in the position adjacent to the carboxylate. A complete reversal in regioselectivity is observed for 1a when treated with LTMP; a sequential process involving a rapid intraaggregate lithiation through a quasi dianion complex "QUADAC" is postulated to explain the unusual reactivity of Me2S2 and I2.