Methanol → Methyl 4-bromo-3-methylbenzoate

To a solution of 4-bromo-3-methylbenzoic acid (Aldrich 532819, 30 g; 139.5 mmol) in MeOH (600 mL), under N2 was added dropwise thionyl chloride (40.5 mL; 558.0 mmol) over 10 min. The reaction mixture was stirred at RT for 12 hours. The solvents were concentrated and the crude residue was dissolved in EtOAc (700 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 (31.3 g, 98%). 1H NMR (DMSO-d6, 300 MHz) δ 7.96-7.95 (m, 1H), 7.79-7.69 (m, 2H), 3.89 (s, 3H), 2.45 (s, 3H). HPLC (Method A) Rt 4.37 min (Purity: 96.4%).

1. concentrationThe solvents were concentrated
2. dissolutionthe crude residue was dissolved in EtOAc (700 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-cbe9e7453c1a4cde8d839a172eaa193b

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08202865B2