Oxalyl chloride → Methyl 5-bromo-3-chloro-2-hydroxy-4-methoxybenzoate

Temperature

13 °C

To a solution of 5-bromo-3-chloro-2-hydroxy-4-methoxybenzoic acid (10.4 g) in dichloromethane (150 mL) were added a solution of oxalyl chloride (7.05 g) in dichloromethane (10 mL) and DMF (3 drops) under ice-cooling, and the mixture was stirred at 13° C. for 1 hr. The solvent was evaporated under reduced pressure, and the residue was dissolved in THF (50 mL). This solution was added dropwise to a solution of triethylamine (1.20 g) in methanol (150 mL) under ice-cooling, and the mixture was stirred at 13° C. for 16 hr. The solvent was evaporated under reduced pressure from the reaction mixture, and the residue was diluted with ethyl acetate and water. 1N Hydrochloric acid was added thereto, and the mixture was partitioned. The organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (10.9 g).

1. temperaturecooling
2. customThe solvent was evaporated under reduced pressure
3. dissolutionthe residue was dissolved in THF (50 mL)
4. additionThis solution was added dropwise to a solution of triethylamine (1.20 g) in methanol (150 mL) under ice-
5. temperaturecooling
6. stirringthe mixture was stirred at 13° C. for 16 hr
7. customThe solvent was evaporated under reduced pressure from the reaction mixture
8. additionthe residue was diluted with ethyl acetate and water
9. addition1N Hydrochloric acid was added
10. customthe mixture was partitioned
11. washThe organic layer was washed with water and saturated brine
12. dry with materialdried over anhydrous sodium sulfate
13. customthe solvent was evaporated under reduced pressure

ORD record

ord-975c21294414492a916dadf3ae7931c9

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09315458B2