Dimethylformamide → Methyl 3-bromo-4-methylbenzoate

Participants

Reaction Steps

To a solution of 2.0 g (9.3 mmol) of 3-bromo-4-methylbenzoic acid in 25 mL of dichloromethane was added 5.6 mL (11.2 mmol) of oxalyl chloride and 100 μL of N,N-dimethylformamide. The resultant mixture was stirred at ambient temperature for 2 hours, concentrated in vacuo, and the residue suspended in methanol. The solution was concentrated in vacuo and the residue purified by flash column chromatography (biotage) using 5% ethyl acetate/hexanes as eluent to provide the title compound. 1H NMR (500 MHz, CDCl3) δ 8.23 (s, 1H), 7.90 (d, 1H, J=8 Hz), 7.33 (d, 1H, J=8 Hz), 3.94 (s, 3H), 2.48 (s, 3H). HPLC/MS (ESI) m/z (M+H)=231.0 (3.63 min).

Provenance & Evidence