Methanol → Methyl 3-bromo-2-fluorobenzoate

To a 100 mL round bottom flask was added 3-bromo-2-fluorobenzoic acid (10.4 g, 47.5 mmol), MeOH (100 mL, 2472 mmol) and sulfuric acid (6 mL, 113 mmol). The reaction mixture was refluxed for 1 hr. After cooling to rt, the MeOH was removed under reduced pressure and the acidic residue was poured into cold water and EtOAc, the layers were separated and the aqueous layer was extracted with EtOAc. The organic layers were combined, washed with brine, dried over NaSO4 and concentrated under reduced pressure to afford 10.02 g of methyl 3-bromo-2-fluorobenzoate. 1H-NMR (400 MHz, DMSO-d6) δ 7.95 (ddd, J=8.1, 6.4, and 1.7 Hz, 1H), 7.82-7.87 (m, 1H), 7.26 (t, J=7.9 Hz, 1H), and 3.86 (s, 3H).

1. temperatureThe reaction mixture was refluxed for 1 hr
2. customthe MeOH was removed under reduced pressure
3. additionthe acidic residue was poured into cold water and EtOAc
4. customthe layers were separated
5. extractionthe aqueous layer was extracted with EtOAc
6. washwashed with brine
7. dry with materialdried over NaSO4
8. concentrationconcentrated under reduced pressure

ORD record

ord-76136f14afca42fc91e39ebd96e6ef5e

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08642759B2