Bromine → 2-Amino-5-bromo-4-chlorobenzoic acid

Temperature

-78 °C

To a solution of 2-amino-4-chlorobenzoic acid (10.0 g, 58.5 mmol) in methanol (150 mL) was added bromine (15.7 mL) at −78° C., and the reaction mixture was stirred at −78° C. for 2 hours. The reaction mixture was quenched with ice water (100 mL) and aq. sodium thiosulfate, and extracted with ethyl acetate (150 mL×3). The organic layers were separated, combined, washed with water (100 mL) and brine (100 mL), dried over sodium sulfate, filtered and concentrated to afford the title compound (9 g, 62%).

1. customThe reaction mixture was quenched with ice water (100 mL) and aq. sodium thiosulfate
2. extractionextracted with ethyl acetate (150 mL×3)
3. customThe organic layers were separated
4. washwashed with water (100 mL) and brine (100 mL)
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-44013421d599483bb0aac41262e9b366

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434700B2