Dichloromethane → 2-Amino-5-bromo-3-chlorobenzoic acid

Reaction equation

[NH2:1][C:2]1C(F)=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:12]N1C(=O)CCC1=O.Cl[CH2:21][Cl:22]>>[NH2:1][C:2]1[C:21]([Cl:22])=[CH:9][C:8]([Br:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 67184N-bromobutanimide

HCID 5864082-Amino-3-fluorobenzoic acid

Product 1

HCID 8279792-Amino-5-bromo-3-chlorobenzoic acidYield 89%

Procedure

To a solution of 2-amino-3-fluorobenzoic acid (10.0 g, 58.5 mmol) in dichloromethane (150 mL) was added N-bromosuccinimide (10.4 g, 58.5 mmol), and the mixture was stirred at room temperature for 2 hours. LCMS showed the reaction was completed. The solid was filtered and washed with dichloromethane (100 mL×3) to give the title compound as a white solid (13.0 g, 89%), which was directly used in the next step without further purification. MS (ES+) C7H5BrClNO2 requires: 249, 251, found: 250, 252 [M+H]+.