Dimethyl Sulfoxide → 3-Bromo-5-(methylthio)benzoic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 3,5-dibromobenzoic acid (2.5 g, 8.9 mmol), sodium methyl sulfide (1.4 g, 20 mmol), and dimethyl sulfoxide (10 mL) was sealed in a microwave tube and heated with an oil bath at 100° C. for 4 h. TLC indicated completion of the reaction. The reaction mixture was poured into water and extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine, dried (Na2SO4), and concentrated. The residue was used for the next step reaction without purification. 1H NMR (400 MHz, CDCl3): δ 7.97 (t, 1H, J=1.6 Hz), 7.87 (t, 1H, J=1.6 Hz), 7.57 (t, 1H, J=1.6 Hz), 2.53 (s, 3H).

Provenance & Evidence