Synthesis of 2-bromopropionic acid

Preparation of 2-bromopropionic acid

Preparation of 2-bromopropionic acid

Preparation of 2-bromopropionic acid

To the round bottom flask fitted with dropping funnel and reflux condenser 50 g of dry propionic acid and 7.6 g of dry amorphous phosphorus are added. From the dropping funnel slowly 66.7 g of bromine are added. When the first portion of bromine is added the mixture is warmed to 40-50° C, and an additional portion of 100 g of bromine from dropping funnel are slowly added. The reaction proceeds rapidly and it is complete by gentle refluxing for 2 hours. 2-Bromopropionyl bromide is distilled at 154° C under atmospheric pressure, yielding 75-80 %.

For the preparation of 2-bromopropionic acid, 2-bromopropionyl bromide is hydrolyzed by addition of one and one-third equivalents of water, the mixture is stirred under a reflux condenser and cooled with ice-water until homogeneous mixture appears. The hydrolysis reaction is complete by warming the reaction mixture for 90 minutes. The crude 2-bromopropionic acid solution is then cooled to room temperature, extracted by treating with several volumes of ether and dried over sodium sulfate. The ether is removed by evaporation and 2-bromopropionic acid is  fractionated in vacuo by collecting fraction boiling at 124° C under a pressure of 18-19 mm. The yield is 60 % based on 2-bromopropionyl bromide. The 2-bromopropionic acid is  hygroscopic and should be protected from the moisture of the air. It is also a powerful skin irritant.

An advanced laboratory manual of organic chemistry, M. Heidelberger, 20-21, 1923

IUPAC Name

2-bromopropanoic acid

InChI

InChI=1S/C3H5BrO2/c1-2(4)3(5)6/h2H,1H3,(H,5,6)

InChI Key

MONMFXREYOKQTI-UHFFFAOYSA-N

Canonical SMILES

CC(C(=O)O)Br

MeSH Synonyms

2-bromopropionic acid, 2-bromopropionic acid, (DL)-isomer, alpha-bromopropionate

Depositor-Supplied Synonyms

2-Bromopropanoic acid, 2-BROMOPROPIONIC ACID, 598-72-1, Propanoic acid, 2-bromo-, Propionic acid, 2-bromo-, 2-bromo-propionic acid, alpha-Bromopropionic acid, .alpha.-Bromopropionic acid, DL-2-Bromopropionic, DL-2-Bromopropionic acid, (+/-)-2-Bromopropionic acid, (S)-(-)-2-BromopropionicAcid, NSC 172, MONMFXREYOKQTI-UHFFFAOYSA-N, EINECS 209-947-6, SBB060286, AI3-52314, Propionic acid, 2-bromo- (6CI,7CI,8CI), DSSTox_CID_7233, DSSTox_RID_78360, DSSTox_GSID_27233, CAS-598-72-1, bromopropionic acid, 2-bromo propionic acid, ACMC-209hub, ACMC-209mgm, methyl bromo acetic acid, AC1L1XZX, Propanoicacid, 2-bromo-, WLN: QVYE1, ACMC-2097mo, AC1Q1LE1, NCIOpen2_009509, SCHEMBL51944, B78300_ALDRICH, (+)-2-bromo-propionic acid, KSC269M4R, 442337_SUPELCO, CCRIS 8896, NSC172, CHEMBL3182324, 18170_FLUKA, CTK1G9648, NSC-172, MolPort-001-783-816, Tox21_201417, Tox21_303226, AC-190, ANW-33380, STL281869, AKOS000119457, AKOS016043520, LS40410, MCULE-3935837943, RP21676, RTR-020736, NCGC00249043-01, NCGC00256941-01, NCGC00258968-01, AN-16055, BC226871, KB-21782, Propanoic acid, 2-bromo-, (.+/-.)-, SC-18426, LS-121233, TR-020736, A5837, B0644, FT-0611604, FT-0642437, FT-0655633, ST51046501, ( inverted exclamation markA)-2-Bromopropionic acid, I04-0584, I04-0898, I04-1124, 3B3-024446, 3B3-034943, 3B3-059148, 3B3-062871, 10327-08-9

Removed Synonyms

(S)-2-bromopropionic acid, (R)-(+)-2-Bromopropionic acid, (S)-(-)-2-Bromopropionic acid, CID11729, 32644-15-8, 10009-70-8

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