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

To a suspension of 4-bromo-3-(trifluoromethyl)benzoic acid (Acceledev 000625, 15 g; 55.76 mmol) in MeOH (300 mL) at RT was added dropwise thionyl chloride (16.18 mL; 223.04 mmol) over 15 min. The reaction mixture was stirred at RT for 12 hours. The solvent 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 (14.80 g, 94%). 1H NMR (DMSO-d6, 300 MHz) δ 8.26 (m, 1H), 8.14-8.13 (m, 2H), 3.93 (s, 3H). HPLC (Method A) Rt 4.71 min (Purity: 99.0%).

1. concentrationThe solvent 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-9c72556d7a62412a920404b9963da819

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08202865B2