Ethyl Acetate → Methyl 5-amino-2-bromobenzoate

Methyl 2-Bromo-5-nitrobenzoate (25.3 g, 97.3 mmol) was dissolved in anhydrous methanol (50 mL), and tin (II) chloride (93.3 g, 487 mmol) was added thereto, and then the reaction mixture was refluxed for 2 hours. After cooling down, ethyl acetate (500 mL) and water (100 mL) were added thereto, and the mixture was neutralized with 4N aqueous NaOH solution, and then it was filtered on celite. The filtrate was concentrated under reduced pressure, and ethyl acetate (200 mL) was added thereto, and then it was washed with saturated NaHCO3 solution (200 mL, twice), water (200 mL) and saturated brine (200 mL) successively. The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure to give the titled reference compound (21.0 g) as a yellow oil. (Yield 94%)

1. temperaturethe reaction mixture was refluxed for 2 hours
2. temperatureAfter cooling down
3. filtrationit was filtered on celite
4. concentrationThe filtrate was concentrated under reduced pressure, and ethyl acetate (200 mL)
5. additionwas added
6. washit was washed with saturated NaHCO3 solution (200 mL
7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
8. customthe solvent was removed under reduced pressure

ORD record

ord-5ee4983d5f4d40caaa7a597d4b0dc862

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08420635B2