Water → Methyl 4-Bromo-2-chlorobenzoate

To a solution of 4-bromo-2-chlorobenzoic acid (450 g) in N,N-dimethylformamide (3000 mL) were added potassium carbonate (792.4 g) and iodomethane (271 g) at 10° C., and the mixture was stirred at the same temperature for 2 hr. Iodomethane (54.3 g) was added, and the mixture was stirred at the same temperature for 1 hr. Iodomethane (27.2 g) was added again, and the mixture was stirred at the same temperature for 1 hr. Iodomethane (27.2 g) was further added, and the mixture was stirred at the same temperature for 1 hr. The reaction mixture was poured into water, and partitioned and extracted with ethyl acetate. The organic layer was washed with 25% brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (477 g) as a pale-yellow oil.

1. stirringthe mixture was stirred at the same temperature for 1 hr
2. stirringthe mixture was stirred at the same temperature for 1 hr
3. stirringthe mixture was stirred at the same temperature for 1 hr
4. custompartitioned
5. extractionextracted with ethyl acetate
6. washThe organic layer was washed with 25% brine
7. dry with materialdried over anhydrous magnesium sulfate
8. customThe solvent was evaporated under reduced pressure

ORD record

ord-5c007da5a14747738342bbf8769eec81

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08114902B2