Sodium Bicarbonate → Methyl 3-amino-6-bromo-2-nitrobenzoate

Methyl 3-acetylamino-6-bromo-2-nitrobenzoate (Reference Compound No. 1-(3) 13.4 g, 42.2 mmol) was dissolved in methanol (240 mL), boron trifluoride diethyl etherate complex (24.0 mL, 190 mmol) was added thereto, and then the mixture was refluxed for 2.5 hours. After the reaction mixture was neutralized with sodium hydrogen carbonate (48 g), the mixture was concentrated under reduced pressure. After ethyl acetate (500 mL) and water (700 mL) were added thereto and the mixture was partitioned, the ethyl acetate layer was washed with water (700 mL) and saturated brine (700 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure to give the titled reference compound (11.6 g) as an orange solid. (Yield 100%)

1. additionboron trifluoride diethyl etherate complex (24.0 mL, 190 mmol) was added
2. temperaturethe mixture was refluxed for 2.5 hours
3. concentrationthe mixture was concentrated under reduced pressure
4. additionAfter ethyl acetate (500 mL) and water (700 mL) were added
5. customthe mixture was partitioned
6. washthe ethyl acetate layer was washed with water (700 mL) and saturated brine (700 mL) successively
7. dry with materialdried over anhydrous magnesium sulfate
8. customthe solvent was removed under reduced pressure

ORD record

ord-7fbd65e3ae58432d89fd788d6b94f5f8

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08551991B2