Hydrochloric Acid → HCID 21476637, compound

Participants

Reaction Steps

4-(Methylsulfonyl)benzoic acid (0.5 g, 2.42 mmol) was suspended in CH2Cl2 (15 mL). Oxalyl chloride (0.44 mL, 4.85 mmol) was added dropwise, followed by addition of two drops of DMF. The reaction mixture was stirred at room temperature for 3 h. CH2Cl2 and the excess of oxalyl chloride were removed under vacuum. The residue was dissolved in CH2Cl2(10 mL) with anisole (0.54 mL, 4.84 mmol). Cooled in an ice bath, aluminum chloride (0.49 g, 3.63 mmol) was added in portions. The mixture was stirred at 0° C. for 2 h, then heated at reflux overnight. Cooled to room temperature, the mixture was poured into 1 N HCl (15 mL) with ice, the pinkish solid was collected and washed with water, hexanes and dried to give 0.50 g (71%) of the title compound (92) as light pink solid. 1H NMR (400 MHz, DMSO-d6): δ 3.28 (s, 3H), 3.85 (s, 3H), 7.09 (d, J=8.8 Hz, 2H), 7.76 (d, J=8.8 Hz, 2H), 7.88 (d, J=8.3 Hz, 2H), 8.07 (d, J=8.2 Hz, 2H). LCMS (ESI): m/z 291 (M+H)+.

Provenance & Evidence