Synthesis of 3-bromobenzoic acid

Preparation of 3-bromobenzoic acid

Preparation of 3-bromobenzoic acid

Preparation of 3-bromobenzoic acid

6 g benzoic acid, 8 g bromine, and about 40 g water are introduced into a tube of thick walled, “hard” glass, which has been sealed and rounded off at one end, and at the other drawn off into as strong as possible a capillary. The tube is heated for about twelve hours at 140-150° C in an air-bath. After the bromination reaction the tube is opened as soon as it gets quite cold in the following way, on account of the high-pressure inside of the tube. By carefully inclining the wrought-iron tube the glass tube is brought so far forward that the capillary just projects from the open end, and it is then heated at its extreme tip until the glass melts. If there is pressure inside, the capillary gets blown out, and a small hole is formed through which the gases escape. This operation must also be carried out in such a manner that if an explosion occurs the fragments of glass cannot endanger anyone. As soon as the gases have escaped, the tube can be taken out from the iron covering, and opened in the usual way by scratching with a file or glass knife and cracking off with a hot glass bead.  If the operation proceeded well the bromine will have almost completely disappeared. The reaction product is washed out of the tube, filtered, rubbed up in a mortar with water, and then boiled in a flask with about 500 ml water for about an hour in order completely to remove unchanged benzoic acid. The solution is finally treated with charcoal and filtered hot; on cooling it deposits the 3-brombenzoic acid in crystalline form. One or two crystallisations from water suffice to render it quite pure. Yield 7 g, melting point 155° C.

Introduction to the preparation of organic compounds, E. Fisher, 17-18, 1909

Preparation of 3-bromobenzoic acid

Preparation of 3-bromobenzoic acid

By the another method a solution containing 4 g of potassium bromate in 150 ml of water is added, with stirring, during 15 min to a solution of o.1 mole of benzoic acid and 2.1 ml of bromine in a mixture of 250 ml of glacial acetic acid and 150 ml of concentrated hydrochloric acid at 25° (cooling!). When the mixture is stirred for a further hour precipitation of m-bromobenzoic acid begins. Then a further 4 g of potassium bromate dissolved in 50 ml of water are dropped in during 30 min. The yield is 11 g.

J. Chem. Soc., 1950, 573-577

IUPAC Name

3-bromobenzoic acid

InChI

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

InChI Key

VOIZNVUXCQLQHS-UHFFFAOYSA-N

Canonical SMILES

C1=CC(=CC(=C1)Br)C(=O)O

Depositor-Supplied Synonyms

3-BROMOBENZOIC ACID, 585-76-2, m-Bromobenzoic acid, 3-BROMBENZOIC ACID, Benzoic acid, 3-bromo-, 3-Bromo-benzoic acid, Benzoic acid, m-bromo-, 3-BROMO BENZENE ACID, VOIZNVUXCQLQHS-UHFFFAOYSA-N, SBB058408, 3-Bromobenzoicacid, 4-Fluorobenzoicacid, NSC 3980, 5-bromobenzoic acid, meta bromobenzoic acid, PubChem3740, ACMC-209m5n, UNII-7DCT3A73LX, AC1L1XE4, AC1Q72YO, SCHEMBL5023, 7DCT3A73LX, M-CARBOXYBENZYLBROMIDE, NCIOpen2_009262, 3-BROMO BENZOIC ACID, 3-Bromobenzenecarboxylic acid, 3-bromophenyl carboxylic acid, BENZOIC ACID,2-BROMO, KSC271O6P, CHEMBL63399, 186295_ALDRICH, RARECHEM AL BO 0037, 16330_FLUKA, Benzoic acid, m-bromo- (8CI), CTK1H1767, NSC3980, MolPort-001-769-109, ACN-S004043, EBD27655, NSC-3980, NSC32739, EINECS 209-562-3, ANW-32985, BBL025793, LABOTEST-BB LT01143269, LABOTEST-BB LT03331369, NSC 32739, NSC-32739, STL377873, AKOS000119769, AM81264, AS01127, LF10862, MCULE-8805391978, PS-5402, RL04207, RP25823, RTR-020353, TRA0027210, NCGC00246888-01, AJ-22410, AK-77039, AN-46117, BC002546, KB-30541, OR004065, SC-05536, TL806158, AB1003659, AI3-08854, DB-024150, ST2410579, TR-020353, B0551, FT-0607488, FT-0615203, ST50319447, A23766, M-6382, 31513-EP2308858A1, 31513-EP2311816A1, 31513-EP2311817A1, 31513-EP2311830A1, AB00973544-04, S01-0184, T5883780, 3B3-013127, F2191-0078, InChI=1/C7H5BrO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4H,(H,9,10

Removed Synonyms

null, m-CARBOXYBENZYL BROMIDE, 2-Chloro-5-fluorobenzoic acid, 5-Fluoro-2-chlorobenzoic acid, BUTTPARK 19\01-68, CID11456, 456-22-4

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