Iodine → Ethyl 5-iodo-2-methylbenzoate

Participants

Reaction Conditions

Reaction Steps

A solution of 5-amino-2-methylbenzoic acid ethyl ester (500 mg, 2.8 mmol) and iodine (425 mg, 1.68 mmol) in toluene (20 ml) was cooled to 0° C. and treated with t-butyl nitrite (303 mg, 2.94 mmol). The reaction mixture was stirred at 0° C. for 1 hour then at room temperature over the weekend. The reaction mixture was washed with 10% aq sodium thiosulphate (20 ml), and brine (20 ml), dried and evaporated. Flash chromatography [silica, iso-hexane/EtOAc, 9:1] gave 5-iodo-2-methylbenzoic acid ethyl ester as a brown oil 510 mg 63%. 1H NMR (CDCl3):1.39 (3H, t, J=12 Hz), 2.53 (3H, s), 4.36 (2H, q, J=12 Hz), 6.97 (1H,d, J=12 Hz), 7.37 (1H, d, J=12 Hz), 8.20 (1H, s).

Provenance & Evidence