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

To a suspension of 4-bromo-3-(trifluoromethyl)benzoic acid (Acceledev 000625, 15.0 g, 55.8 mmol) in MeOH (300 mL) at RT was added dropwise thionyl chloride (16.2 mL, 223.0 mmol) over 15 minutes. The reaction mixture was stirred at RT for 12 hours. The reaction mixture was concentrated and the crude residue was diluted with EtOAc (500 mL). The organic layer was washed with a saturated aqueous solution of NaHCO3 (200 mL), water (200 mL), brine (200 mL), dried over MgSO4 and concentrated affording the title compound as an orange solid (14.8 g, 94%). 1H NMR (DMSO-d6, 300 MHz) δ 8.26 (m, 1H), 8.14 (m, 2H), 3.93 (s, 3H). HPLC (Method A) Rt 4.71 min (Purity: 99.0%).

1. concentrationThe reaction mixture was concentrated
2. additionthe crude residue was diluted with EtOAc (500 mL)
3. washThe organic layer was washed with a saturated aqueous solution of NaHCO3 (200 mL), water (200 mL), brine (200 mL)
4. dry with materialdried over MgSO4
5. concentrationconcentrated

ORD record

ord-6d9216c01be44b7596c8b2d1cc6efa25

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08802704B2