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-11731b27b9f746e1bd0deec605db969c

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07994185B2