Water → Methyl 3-amino-2-bromobenzoate

2-Bromo-3-nitro-benzoic acid methyl ester (12.9 g, 49.5 mmol) (prepared from 2-amino-3-nitro-benzoic acid as described by Webber E. S., et al., see patent application number WO 01/16136 A2) and SnCl2 (42 g, 223 mmol) were refluxed in methanol (225 mL, 0.2 M) and H2O (5.3 g, 243 mmol) for 2 hours. After cooling at ambient temperature, diatomaceous earth (20 g) and dichloromethane (1 L) were added followed with 3N aqueous sodium hydroxide (150 mL) with vigorous stirring. The mixture was filtered and the organic phase was washed with saturated aqueous sodium chloride. The organic solution was dried over sodium sulfate, filtered and all volatiles were removed under reduced pressure to afford Intermediate 5(a) (11.4 g) in 98% yield.

1. filtrationThe mixture was filtered
2. washthe organic phase was washed with saturated aqueous sodium chloride
3. dry with materialThe organic solution was dried over sodium sulfate
4. filtrationfiltered
5. customall volatiles were removed under reduced pressure

ORD record

ord-38bf6de184c3462982577889b87ed83e

Source dataset

uspto-grants-2005_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06967198B2