Methanol → Methyl 4-bromo-3-(trifluoromethyl)benzoate

To a suspension of 4-bromo-3-(trifluoromethyl)benzoic acid (APAC Pharmaceuticals, 20 g, 74.35 mmol) in MeOH (400 ml) at 0° C. was added thionyl chloride (21.6 ml, 297 mmol) dropwise. The reaction mixture was stirred at RT for 24 hours. The solvent was concentrated under vacuum and the crude residue was diluted with EtOAc (250 mL). The organic layer was washed with a saturated NaHCO3 solution (100 mL), water (100 mL), brine (100 mL), dried over MgSO4, filtered off and concentrated under vacuum to afford the title compound as a yellow solid (19.13 g, 91%). HPLC (Method A) Rt 5.12 min (Purity: 99.2%).

1. concentrationThe solvent was concentrated under vacuum
2. additionthe crude residue was diluted with EtOAc (250 mL)
3. washThe organic layer was washed with a saturated NaHCO3 solution (100 mL), water (100 mL), brine (100 mL)
4. dry with materialdried over MgSO4
5. filtrationfiltered off
6. concentrationconcentrated under vacuum

ORD record

ord-c92fdce892274951ad0462f09194b036

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08802704B2