Isoamyl Nitrite → 4-Cyano-3-iodo-5-trifluoromethyl-thiophene-2-carboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

Combine 3-amino-4-cyano-5-trifluoromethyl-thiophene-2-carboxylic acid ethyl ester, prepared in preparation 45, (1.12 mmol), diiodomenthane (3.92 mmol), and isoamyl nitrite (2.8 mmol) in CH3CN and heat to 80° C. After 45 minutes, cool to room temperature and concentrate in vacuo. Purify the dark residue by flash chromatography eluting with methylene chloride. Concentration of desired fractions and recrystallization from hexanes provides the title compound: 1H NMR (400 MHz, CDCl3) δ 4.45 (q, 2H, J=7.2 Hz) and 1.44 (t, 3H, J=7.3 Hz), 19F NMR (CDCl3) δ—57.6 ppm (s).

Provenance & Evidence