Diethyl Ether → Methyl 5-amino-2-bromo-4-chlorobenzoate

Participants

Reaction Conditions

Reaction Steps

Methyl 3-amino-4-chlorobenzoate (Reference Compound No. 9, 12.0 g, 64.7 mmol) was dissolved in N,N-dimethylformamide (250 mL), and after cooling down to 0° C., N-bromosuccinimide (11.5 g, 64.6 mmol) was added thereto, and then the reaction mixture was stirred under argon atmosphere at room temperature for 30 minutes. Ethyl acetate (200 mL) and diethyl ether (200 mL) were added to the reaction mixture and then the whole was washed with 1% aqueous sodium hyposulfite solution (500 mL). The aqueous layer was extracted with ethyl acetate/diethylether (1/1) (200 mL). The combined organic layer was washed with water (400 mL, 4 times) and saturated brine (300 mL) successively, dried over anhydrous magnesium sulfate and then the solvent was removed under reduced pressure. The obtained residue was filtered with hexane (15 mL) to give the titled reference compound (15.74 g) as a pale brown solid. (Yield 92%)

Provenance & Evidence