88-65-3

Basic information

• Product Name: 2-Bromobenzoic acid
• Synonyms: o-bromo-benzoicaci;2-Bromobenzoic aicd;2-Brom-benzoic acid;Brombenzoicacid,95%;2-Bromobenzene carboxylic acid;o-Bromobenzoic Acid 2-Bromobenzoic Acid;O-BROMOBENZOIC ACID CRYSTALLINE;2-BROMO BENZOIC ACID FOR SYNTHESIS
• CAS NO: 88-65-3
• Molecular Formula: C₇H₅BrO₂
• Molecular Weight: 201.02
• EINECS: 201-848-6
• Product Categories: Aromatic Compounds;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic acid;Organic acids;Acids & Esters;Bromine Compounds;C7;Carbonyl Compounds;Carboxylic Acids;alkyl bromide| carboxylic acid
• Mol File: 88-65-3.mol
• Article Data: 104

Chemical Properties

• Melting Point: 147-150 °C(lit.)
• Boiling Point: 296.4 °C at 760 mmHg
• Flash Point: >100°C
• Appearance: White to light yellow or beige/Powder
• Density: 1,929 g/cm3
• Vapor Pressure: >1 mm Hg ( 20 °C)
• Refractive Index: 1.6080 (estimate)
• Storage Temp.: Room temperature.
• Solubility: 95% ethanol: soluble100mg/mL, clear, colorless to yellow
• PKA: 2.84(at 25℃)
• Water Solubility: slightly soluble
• BRN: 971266
• CAS DataBase Reference: 2-Bromobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromobenzoic acid(88-65-3)
• EPA Substance Registry System: 2-Bromobenzoic acid(88-65-3)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-36-37/38-22
• Safety Statements: 26-36-24/25-37/39
• WGK Germany: 3
• RTECS: DG4448035
• TSCA: Yes
• Hazardous Substances Data: 88-65-3(Hazardous Substances Data)

Usage

Chemical Properties

White to light yellow crystal powder

Uses

2-Bromobenzoic acid was used in the synthesis of new zinc(II) ? 2-bromobenzoate complex compounds. It was used as the starting reagent in the synthesis of hemilabile benzimidazolyl phosphine ligands.

Synthesis Reference(s)

Canadian Journal of Chemistry, 43, p. 1306, 1965 DOI: 10.1139/v65-178The Journal of Organic Chemistry, 59, p. 4042, 1994 DOI: 10.1021/jo00094a007

General Description

2-Bromobenzoic acid (2-BA) on condensation with aminoquinolines yields phenylquinolylamines. 2-BA is the common building block for synthesis of various nitrogen heterocycles.

Purification Methods

Crystallise the acid from *C6H6 or MeOH. The anilide has m 141o (from EtOH/H2O). [Beilstein 9 IV 1011.]

InChI:InChI=1/C7H5BrO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,(H,9,10)/p-1

Synthetic route

2-bromobenzoic acid methyl ester (610-94-6) → 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
With water; sodium hydroxide In ethanol at 10 - 20℃; for 1.08333h;	100%
With iodine; aluminium In acetonitrile at 80℃; for 18h;	99%

1-(2-bromophenyl)-4,4,4-trifluorobutane-1,3-dione (23975-63-5) → 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
With oxygen; sodium hydrogencarbonate In acetonitrile for 4h; Molecular sieve; Irradiation;	96%

2-methylphenyl bromide (95-46-5) → 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
With ruthenium trichloride; sodium hypochlorite; tetrabutylammomium bromide In 1,2-dichloro-ethane at 25℃; for 2h;	95%
With ruthenium trichloride; sodium hypochlorite; tetrabutylammomium bromide In 1,2-dichloro-ethane at 25℃; for 2h; Rate constant; pH 9;	95%
With potassium acetate In water	93.2%

ortho-bromobenzaldehyde (6630-33-7) → 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
With oxygen; Langlois reagent In acetonitrile at 25℃; under 760.051 Torr; for 12h; Irradiation; Green chemistry;	95%
With tert.-butylhydroperoxide; potassium tert-butylate In water at 60℃; for 5h;	90%
With oxygen at 120℃; for 5h; Neat (no solvent);	85%

o-bromobenzyl alcohol (18982-54-2) → 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
With sodium bromate; sodium hydrogen sulfate In acetonitrile for 20h; Heating;	95%
With Langlois reagent In acetonitrile at 25℃; for 12h; Irradiation; Sealed tube;	91%
With 3,5-Lutidine; 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl; sodium persulfate; tris(2,2'‐bipyridine)ruthenium(II) hexafluorophosphate In water; acetonitrile at 20℃; for 48h; Sealed tube; Irradiation;	75%

2-bromostyrene (2039-88-5) → 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
Stage #1: 2-bromostyrene With tert.-butylhydroperoxide; iron(III) chloride hexahydrate; sodium hydroxide In water at 80℃; for 10h; Stage #2: With hydrogenchloride In water at 20℃;	95%
With Oxone; 2-iodo-3,4,5,6-tetramethylbenzoic acid In water; acetonitrile for 24h;	81%
With Oxone In water; acetonitrile for 24h; Reflux;	77%

1-(2-bromophenyl)-1,2-ethanediol → 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
With tert.-butylhydroperoxide; potassium tert-butylate In water at 80℃; for 8h;	94%

2-methylphenyl bromide (95-46-5) + water (7732-18-5) → 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
With potassium bromide; potassium acetate	92.7%

2-(2-bromophenyl)-2-oxoacetaldehyde → 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
With iodine; dimethyl sulfoxide at 180℃; for 0.0833333h; Inert atmosphere; Microwave irradiation;	92%

C12H13BrOS2 → 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
With sodium hydroxide In water at 100℃; for 9h; Reflux; chemoselective reaction;	92%

ortho-bromobenzaldehyde (6630-33-7) → o-bromobenzyl alcohol (18982-54-2) + 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
Stage #1: ortho-bromobenzaldehyde With potassium hydroxide for 0.0833333h; Cannizzaro Reaction; Milling; Inert atmosphere; Sealed tube; Green chemistry; Stage #2: With hydrogenchloride In water for 0.0833333h; Green chemistry;	A 91% B 90%

5-[(2-bromophenyl)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione (15795-61-6) → 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
With oxone In water for 16h; Reflux;	91%

2-bromo-N,N-diisopropylbenzamide (79839-66-0) → 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
With hydrogenchloride; zinc(II) chloride at 160℃; for 72h;	90%

2-bromo-N-(2-(pyridin-2-yl)propan-2-yl)benzamide → 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
With hydrogenchloride In water at 145℃; for 48h; Schlenk technique;	89%
With hydrogenchloride; water at 145℃; for 48h;	80%

2-bromophenyl methyl ketone (2142-69-0) → 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
With Oxone; trifluoroacetic acid In 1,4-dioxane for 10h; Reflux; Green chemistry;	88%
With hydroxylamine hydrochloride; iodine In dimethyl sulfoxide at 100℃; for 5h;	58%

1-Bromo-2-iodobenzene (583-55-1) + carbon monoxide (201230-82-2) → 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
With C22H28Br2N4Pd; water; potassium carbonate In tetrahydrofuran at 100℃; under 750.075 Torr; for 24h; Autoclave;	86%
With water; palladium diacetate; potassium carbonate at 20℃; under 760.051 Torr; for 12h;	84%
With water; palladium diacetate; triethylamine; triphenylphosphine In 1,4-dioxane at 110℃; under 11251.1 Torr; for 2h; Flow reactor;	70%

2-(2-bromophenyl)-2-hydroxyacetonitrile (52923-21-4, 1269472-47-0, 548478-30-4) → ortho-bromobenzaldehyde (6630-33-7) + 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
Stage #1: 2-(2-bromophenyl)-2-hydroxyacetonitrile With (η(6)-benzene)chloro[1,2-bis(diphenylphosphino)ethane]ruthenium(II) chloride In benzene at 120℃; for 24h; Inert atmosphere; Schlenk technique; Stage #2: With water In dichloromethane; ethyl acetate; benzene for 24h;	A 81% B 17%

1-Bromo-2-bromomethyl-benzene (3433-80-5) → 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
With Oxone In water; acetonitrile for 24h; Reflux;	80%

2,5-dibromobenzoic acid (610-71-9) → m-bromobenzoic acid (585-76-2) + benzoic acid (65-85-0) + 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
With n-butyllithium In tetrahydrofuran	A 78% B 13% C 2%

2-methylphenyl bromide (95-46-5) → 1-Bromo-2-bromomethyl-benzene (3433-80-5) + 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
With tert.-butylhydroperoxide; copper(ll) bromide In acetic anhydride	A 77% B 10%

1-(Bis-tert-butylperoxy-methyl)-2-bromo-benzene (106914-56-1) → 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
With piperidine In water at 90℃; for 3h;	76%

2-b romo-N-(quinolin-8-yl)benzamide → 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
Stage #1: 2-b romo-N-(quinolin-8-yl)benzamide With ozone In dichloromethane at -78℃; Inert atmosphere; Stage #2: With lithium hydroxide monohydrate; dihydrogen peroxide In tetrahydrofuran; water at 20℃; for 24h; Inert atmosphere;	66%

benzoic acid (65-85-0) → 2,6-dibromobenzoic acid (601-84-3) + 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
Stage #1: With [bis(acetoxy)iodo]benzene; iodine In 1,2-dichloro-ethane at 20℃; for 1h; Stage #2: benzoic acid With tetrabutylammomium bromide; palladium diacetate In 1,2-dichloro-ethane at 100℃; for 24h;	A n/a B 65%

carbon dioxide (124-38-9) + (2-bromophenyl)boronic acid (244205-40-1) → 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); potassium methanolate In N,N-dimethyl acetamide at 70℃; for 24h; Schlenk technique; Sealed tube;	65%

o-bromobenzyl alcohol (18982-54-2) → ortho-bromobenzaldehyde (6630-33-7) + 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
With tert.-butylhydroperoxide; [O-Cu4(triethanolamine)4(BOH)4][BF4]2 In acetonitrile at 69.84℃; for 6h;	A 61.8% B n/a
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; Ir(4,4'-di-tert-butyl-2,2'-bipyridyl)(2-phenylpyridine)2(PF6); tetrabutyl-ammonium chloride; oxygen; sodium hydrogencarbonate In dichloromethane; water at 20℃; for 48h; Reagent/catalyst; Solvent; Irradiation; Green chemistry; chemoselective reaction;	A > 99 %Chromat. B 9%
With oxygen; potassium carbonate In water at 80℃; for 48h;

4-(2-bromophenyl)but-3-en-2-one (72454-54-7) → 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
With hydroxylamine hydrochloride; iodine In dimethyl sulfoxide at 100℃; for 6h;	60%

1-Bromo-2-iodobenzene (583-55-1) + diphenylmethylsilanecarboxylic acid (18414-58-9) → 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
With potassium trimethylsilonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 60℃; Sealed tube;	60%

benzoic acid (65-85-0) → 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
With 1,2-dibromo-1,1,2,2-tetrachloroethane; N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In tetrahydrofuran; hexane; cyclohexane 1.) -90 deg C, 60 min, 2.) -78 deg C;	55%
With 1,2-dibromo-1,1,2,2-tetrachloroethane; N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In tetrahydrofuran 1.) -90 deg C, 30 min, 2.) -78 deg C;	55%
With chlorosulfonic acid; bromine at 10℃; for 2.5h; Temperature; Inert atmosphere;

1-Bromo-2-iodobenzene (583-55-1) + carbon monoxide (201230-82-2) + phenylboronic acid (98-80-6) → o-bromobenzophenone (13047-06-8) + 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
With C57H43IP2Pd; potassium carbonate In 1,4-dioxane at 90℃; under 3750.38 Torr; for 12h; carbonylative Suzuki coupling; Autoclave;	A 50% B n/a

1-(2-bromophenyl)-butane-1,3-dione (57279-20-6) → 2-bromobenzoic-acid (88-65-3)

Conditions	Yield
With oxygen; sodium hydrogencarbonate In acetonitrile for 4h; Molecular sieve; Irradiation;	50%

2-bromobenzoic-acid (88-65-3) → 2-bromobenzoic acid chloride (7154-66-7)

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 3h;	100%
Stage #1: 2-bromobenzoic-acid With oxalyl dichloride In dichloromethane at 20℃; for 0.0833333h; Stage #2: With N,N-dimethyl-formamide In dichloromethane at 20℃; for 5h;	100%
With thionyl chloride In N,N-dimethyl-formamide at 70℃; Inert atmosphere;	100%

2-bromobenzoic-acid (88-65-3) → 2-bromobenzoic anhydride (49619-44-5)

Conditions	Yield
With trimethylsilylethoxyacetylene In dichloromethane at 20℃; for 3h;	100%
With potassium carbonate In dichloromethane at 20℃; for 0.583333h;	91%
With potassium carbonate; p-toluenesulfonyl chloride In acetonitrile at 20℃; for 2h;	70%

anthranilic acid (118-92-3) + 2-bromobenzoic-acid (88-65-3) → Vanadox (579-92-0)

Conditions	Yield
With copper(I) oxide; copper; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 20h; Inert atmosphere;	100%
With copper; potassium carbonate; copper(II) oxide In N,N-dimethyl-formamide at 130℃; for 20h;	94%
With copper; potassium carbonate In N,N-dimethyl-formamide Jourdan-Ullmann reaction; Inert atmosphere; Reflux;	91%

2-amino-3-methoxybenzoic acid (3177-80-8) + 2-bromobenzoic-acid (88-65-3) → 2-(2-carboxyphenylamino)-3-methoxybenzoic acid (88377-32-6)

Conditions	Yield
With copper; potassium carbonate In ethanol for 1h; Reflux; Inert atmosphere;	100%
With copper; potassium carbonate In ethanol for 1.5h; Reflux;	5.07 g
With copper; potassium carbonate In ethanol for 1.5h; Reflux;

2-bromobenzoic-acid (88-65-3) → 1,2-dibromobenzene (583-53-9)

Conditions	Yield
With dibromoisocyanuric acid In dichloromethane at 20℃; for 24h; Reagent/catalyst; Solvent; Temperature; UV-irradiation;	100%

methanol (67-56-1) + 2-bromobenzoic-acid (88-65-3) → 2-bromobenzoic acid methyl ester (610-94-6)

Conditions	Yield
With sulfuric acid Reflux; Inert atmosphere;	99%
With sulfuric acid Reflux;	99%
With sulfuric acid at 0℃; for 20.25h; Fischer-Speier Esterification; Reflux;	96%

phenylboronic acid (98-80-6) + 2-bromobenzoic-acid (88-65-3) → 2-Biphenylcarboxylic acid (947-84-2)

Conditions	Yield
With trans-[PdBr2(1-n-butyl-3-(1-O-methyl-6-deoxy-α-D-glucopyrano-6-yl)imidazol-2-ylidene)2]; sodium methylate In water at 100℃; for 15h; Suzuki coupling;	99%
With potassium carbonate In water at 50℃; for 1.5h; Suzuki Coupling;	98%
With magnesium hydroxide; potassium hydroxide; barium(II) hydroxide; calcium hydroxide In water at 20℃; for 15h; Suzuki Coupling;	98%

1,3-cylohexanedione (504-02-9) + 2-bromobenzoic-acid (88-65-3) → 2-bromo-benzoic acid 3-oxo-cyclohex-1-enyl ester (252679-98-4)

Conditions	Yield
With 2-chloro-1-methyl-pyridinium iodide; triethylamine In tetrahydrofuran at 20℃; Acylation;	99%
With 2-chloro-1-methyl-pyridinium iodide; triethylamine In tetrahydrofuran at 20℃; for 10h;	99%

4-Methoxybenzenethiol (696-63-9) + 2-bromobenzoic-acid (88-65-3) → 2-<(4-methoxyphenyl)thio>benzoic acid (19862-91-0)

Conditions	Yield
With copper(I) oxide; copper; potassium carbonate In 2-ethoxy-ethanol at 130℃; for 4h;	99%

Hexanethiol (111-31-9) + 2-bromobenzoic-acid (88-65-3) → 2-(hexylthio)benzoic acid (15823-57-1)

Conditions	Yield
With copper(I) oxide; copper; potassium carbonate In 2-ethoxy-ethanol at 130℃; for 12h;	99%

thiophenol (108-98-5) + 2-bromobenzoic-acid (88-65-3) → 2-(phenylthio)benzoic acid (1527-12-4)

Conditions	Yield
With copper(I) oxide; copper; potassium carbonate In 2-ethoxy-ethanol at 130℃; for 4h;	99%
With tetra(n-butyl)ammonium hydroxide In water at 80℃; for 48h; Inert atmosphere; Sealed tube; chemoselective reaction;	87%
With copper(I) oxide; copper; potassium carbonate In 2-ethoxy-ethanol at 130℃; for 4h;	76%

benzamidine monohydrochloride (1670-14-0) + 2-bromobenzoic-acid (88-65-3) → 2-phenyl-4(3H)-quinazolinone (1022-45-3)

Conditions	Yield
With C26H24Cu2N8(2+)*2F6P(1-); caesium carbonate In N,N-dimethyl-formamide at 70℃; for 6h; Inert atmosphere; Sealed tube;	99%
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 10h; Inert atmosphere; Sealed tube;	95%
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 25℃; for 12h; Inert atmosphere;	85%

3-nitro-aniline (99-09-2) + 2-bromobenzoic-acid (88-65-3) → 2-bromo-N-(3-nitrophenyl)benzamide (316139-21-6)

Conditions	Yield
Stage #1: 2-bromobenzoic-acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 20h; Inert atmosphere; Cooling with ice; Stage #2: 3-nitro-aniline With pyridine In dichloromethane at 45℃; for 1h; Inert atmosphere;	99%
Stage #1: 2-bromobenzoic-acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide for 20h; Sealed tube; Inert atmosphere; Cooling with ice; Stage #2: 3-nitro-aniline With pyridine In dichloromethane; N,N-dimethyl-formamide at 45℃; for 1h;	99%

p-tolylboronic pinacol ester (195062-57-8) + 2-bromobenzoic-acid (88-65-3) → o-tolylbenzoic acid (7148-03-0)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium hydroxide In neat (no solvent) at 110℃; for 24h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;	99%

4-iodoanisol (529-28-2) + bicyclo[2.2.1]hepta-2,5-diene (121-46-0) + 2-bromobenzoic-acid (88-65-3) → 1-methoxyphenanthrene (834-99-1)

Conditions	Yield
With palladium diacetate; caesium carbonate; tricyclohexylphosphine In 1,4-dioxane at 130℃; for 18h; Schlenk technique; Sealed tube; Inert atmosphere;	99%

bicyclo[2.2.1]hepta-2,5-diene (121-46-0) + 1-iodo-2-(trifluoromethoxy)benzene (175278-00-9) + 2-bromobenzoic-acid (88-65-3) → 1-(trifluoromethoxy)phenanthrene

Conditions	Yield
With palladium diacetate; caesium carbonate; tricyclohexylphosphine In 1,4-dioxane at 130℃; for 18h; Schlenk technique; Sealed tube; Inert atmosphere;	99%

1-Fluoro-2-iodobenzene (348-52-7) + bicyclo[2.2.1]hepta-2,5-diene (121-46-0) + 2-bromobenzoic-acid (88-65-3) → 1-fluorophenanthrene (440-38-0)

Conditions	Yield
With palladium diacetate; caesium carbonate; tricyclohexylphosphine In 1,4-dioxane at 130℃; for 18h; Schlenk technique; Sealed tube; Inert atmosphere;	99%

ethyl 5-(2-iodophenoxy)pentanoic acid (132902-33-1) + bicyclo[2.2.1]hepta-2,5-diene (121-46-0) + 2-bromobenzoic-acid (88-65-3) → ethyl 5-(phenanthren-1-yloxy)pentanoate

Conditions	Yield
With palladium diacetate; caesium carbonate; tricyclohexylphosphine In 1,4-dioxane at 130℃; for 18h; Schlenk technique; Sealed tube; Inert atmosphere;	99%

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) + 2-bromobenzoic-acid (88-65-3) → 2-((2-bromobenzyl)oxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions	Yield
In neat (no solvent) at 30℃; Inert atmosphere; Schlenk technique; Glovebox; chemoselective reaction;	99%
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In neat (no solvent) at 60℃; for 24h;
With (4-Me)Triaz(NHPiPr2)2Mn(CO)2Br In toluene at 25℃; for 6h; Catalytic behavior; Inert atmosphere; chemoselective reaction;	> 99 %Spectr.

2-(2-iodophenyl)-1-methyl-1H-indole + 2-bromobenzoic-acid (88-65-3) → 9-methyl-9H-dibenzo[a,c]carbazole (54880-07-8)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; p-benzoquinone In dimethyl sulfoxide at 140℃; for 9h; Schlenk technique; Inert atmosphere;	99%

2-isopropyliodobenzene (19099-54-8) + 2-bromobenzoic-acid (88-65-3) → 1-isopropyltriphenylene

Conditions	Yield
With norborn-2-ene; bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; p-benzoquinone In dimethyl sulfoxide at 140℃; for 3h; Schlenk technique; Inert atmosphere;	99%

ethyl acetoacetate (141-97-9) + 2-bromobenzoic-acid (88-65-3) → 2-(ethoxycarbonylmethyl)benzoic acid (22479-46-5)

Conditions	Yield
Stage #1: ethyl acetoacetate With sodium ethanolate In ethanol at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 2-bromobenzoic-acid With copper(I) bromide In ethanol at 80℃; for 16h; Inert atmosphere;	98%
With sodium ethanolate; copper

Indole-3-carboxaldehyde (487-89-8) + 2-bromobenzoic-acid (88-65-3) → N-(o-bromobenzoyl)indole-3-carboxaldehyde

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran Ambient temperature;	98%

Thiosalicylic acid (147-93-3) + 2-bromobenzoic-acid (88-65-3) → 2,2'-thiodibenzoic acid (22219-02-9)

Conditions	Yield
With potassium carbonate; copper In water at 130 - 140℃; for 3h; Product distribution / selectivity; Ullmann Condensation;	98%
With copper; potassium carbonate In water at 130 - 140℃; for 3h;	96%
With potassium carbonate In water	52.8 g (97%)

2-bromobenzoic-acid (88-65-3) → salicylic acid (69-72-7)

Conditions	Yield
Stage #1: 2-bromobenzoic-acid With water; sodium carbonate for 1h; Heating / reflux; Stage #2: With water; trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(ll) bromide at 80℃; for 1h; Stage #3: With hydrogenchloride In water at 25℃; Product distribution / selectivity;	98%
Stage #1: 2-bromobenzoic-acid With water; sodium carbonate for 1h; Heating / reflux; Stage #2: trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(I) bromide In acetonitrile at 80℃; for 2h; Stage #3: With hydrogenchloride In water; acetonitrile at 25℃; Product distribution / selectivity;	98%
Stage #1: 2-bromobenzoic-acid With water; sodium carbonate at 80℃; Stage #2: With water; trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(I) bromide In water; acetonitrile at 80℃; for 3h; Stage #3: With hydrogenchloride In water; acetonitrile at 20℃; Product distribution / selectivity;	96%

1-(pyridin-2-yl)hept-2-yn-1-ol (934399-67-4) + 2-bromobenzoic-acid (88-65-3) → C19H18BrNO2 (1256742-75-2)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;	98%

[3-(methoxycarbonyl)phenyl]boronic acid (99769-19-4) + 2-bromobenzoic-acid (88-65-3) → 3'-(methoxycarbonyl)-[1,1'-biphenyl]-2-carboxylic acid (171905-91-2)

Conditions	Yield
With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium carbonate In chloroform; water at 80 - 100℃; for 0.25h; Suzuki Coupling;	98%
With PdCl2-[5-(naphth-1-yl)isoxazole-3-carbaldehyde oxime]; potassium carbonate In methanol; water at 100℃; for 0.166667h; Suzuki Coupling;	97%

ortho-methylphenyl iodide (615-37-2) + bicyclo[2.2.1]hepta-2,5-diene (121-46-0) + 2-bromobenzoic-acid (88-65-3) → 1-methylphenanthrene (832-69-9)

Conditions	Yield
With palladium diacetate; caesium carbonate; tricyclohexylphosphine In 1,4-dioxane at 130℃; for 18h; Catalytic behavior; Reagent/catalyst; Solvent; Schlenk technique; Sealed tube; Inert atmosphere;	98%

2-iodo-5-methylthiophene (16494-36-3) + bicyclo[2.2.1]hepta-2,5-diene (121-46-0) + 2-bromobenzoic-acid (88-65-3) → 2-methylnaphtho[2,1-b]thiophene (16587-35-2)

Conditions	Yield
With palladium diacetate; caesium carbonate; tricyclohexylphosphine In 1,4-dioxane at 130℃; for 18h; Schlenk technique; Sealed tube; Inert atmosphere;	98%

Upstream product

• 87-25-2 2-ethoxycarbonylaniline 
• 110-00-9 furan 
• 1608-42-0 benzenedizolium-2-carboxylate 
• 55566-61-5 2-(2-anilino-[1]naphthylazo)-benzoic acid 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 18982-54-2 o-bromobenzyl alcohol 
• 6630-33-7 ortho-bromobenzaldehyde 
• 4885-28-3 3-H-8-bromo-4-methyl-3,4-azabora-isochinoline 
• 72454-54-7 4-(2-bromophenyl)but-3-en-2-one 
• 95-56-7 2-hydroxybromobenzene 
• 201230-82-2 carbon monoxide 
• 6091-64-1 2-bromobenzoic acid ethyl ester 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 22479-46-5 2-(ethoxycarbonylmethyl)benzoic acid 
• 2042-37-7 o-cyanobromobenzene 
• 59142-63-1 2-bromo-4'-methoxy-benzophenone 
• 13275-42-8 2-(2-bromophenyl)-benzimidazole 
• 52962-28-4 2-(bis-ethoxycarbonyl-methyl)-benzoic acid 
• 1139-83-9 urolithin B 
• 91-40-7 2-(phenylamino)benzoic acid 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 7154-66-7 2-bromobenzoic acid chloride 
• 6091-64-1 2-bromobenzoic acid ethyl ester 
• 857588-60-4 N-(2,3-dimethoxy-phenyl)-anthranilic acid 
• 873387-02-1 N-(2-arsono-phenyl)-anthranilic acid 
• 132106-18-4 1-benzoyloxy-2-(2-bromo-benzoyloxy)-ethane 

Relevant articles and documents

Combining photoredox catalysis and oxoammonium cations for the oxidation of aromatic alcohols to carboxylic acids

A methodology is reported for converting alcohols to the corresponding carboxylic acids. A dual catalytic system involving a merger of photoredox catalysis and 4-acetamido-TEMPO is employed to carry out this oxidation process.

One-Pot Direct Oxidation of Primary Amines to Carboxylic Acids through Tandem ortho-Naphthoquinone-Catalyzed and TBHP-Promoted Oxidation Sequence

Biomimetic oxidation of primary amines to carboxylic acids has been developed where the copper-containing amine oxidase (CuAO)-like o-NQ-catalyzed aerobic oxidation was combined with the aldehyde dehydrogenase (ALDH)-like TBHP-mediated imine oxidation protocol. Notably, the current tandem oxidation strategy provides a new mechanistic insight into the imine intermediate and the seemingly simple TBHP-mediated oxidation pathways of imines. The developed metal-free amine oxidation protocol allows the use of molecular oxygen and TBHP, safe forms of oxidant that may appeal to the industrial application.