Bromine → 2-Amino-5-bromo-4-chlorobenzoic acid
Reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:12]Br>CO>[NH2:1][C:2]1[CH:10]=[C:9]([Cl:11])[C:8]([Br:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
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%).
Workup
- customThe reaction mixture was quenched with ice water (100 mL) and aq. sodium thiosulfate
- extractionextracted with ethyl acetate (150 mL×3)
- customThe organic layers were separated
- washwashed with water (100 mL) and brine (100 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-44013421d599483bb0aac41262e9b366
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434700B2
Reaction notes
Loading…