Diiodomethane → 4-Tert-butyl-phenyl-4-cyano-5-iodo-thiophene-2-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

Combine 5-amino-3-(4-tert-butyl-phenyl)-4-cyano-thiophene-2-carboxylic acid methyl ester (0.29 mmol) in acetonitrile and add diiodomethane (1.02 mmol) and iso-amyl nitrite (0.73 mmol) and heat to 100° C. After 15 minutes, cool the reaction slowly to room temperature and stir an additional 1 hour. Concentrate the reaction to a dark oil which is purified by radial chromatography on a 2000 micron silica plate eluting with 50/50 methylene chloride/hexane and then 100% methylene chloride. Concentrate desired fractions were to give the title compound. 1H NMR (400 MHz, CDCl3) δ 7.41 (m, 4H), 3.78 (s, 3H), 1.37 (s, 9H).

Provenance & Evidence