Acetic Acid → (4-Amino-3-bromophenyl)acetic acid

Reaction equation

C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=[O:13])=[CH:7][C:6]=1[Br:15])(=O)C.[OH-].[Na+].C(O)(=O)C>Cl>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=[O:13])=[CH:7][C:6]=1[Br:15]

Participants

Procedure

30.5 g (0.112 mole) of 4-acetamido-3-bromophenylacetic acid are heated to 100° C. in 100 ml of 6 N hydrochloric acid until a clear solution forms, and the mixture is subsequently kept at 110° C. for one hour. Cooling is effected, followed by rendering alkaline with a solution of sodium hydroxide and acidifying with glacial acetic acid. The thus-formed flocculent precipitate is suction filtered, washed with water and dried to obtain 23.5 g (91.4% of theory) of 4-amino-3-bromophenylacetic acid (m.p. 139° to 140° C.).