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

Temperature

0 °C

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%)

1. washthe whole was washed with 1% aqueous sodium hyposulfite solution (500 mL)
2. extractionThe aqueous layer was extracted with ethyl acetate/diethylether (1/1) (200 mL)
3. washThe combined organic layer was washed with water (400 mL, 4 times) and saturated brine (300 mL) successively
4. dry with materialdried over anhydrous magnesium sulfate
5. customthe solvent was removed under reduced pressure
6. filtrationThe obtained residue was filtered with hexane (15 mL)

ORD record

ord-0376188696a843c18bc0bc0b4316cc69

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08420635B2