Triethylamine → Ethyl 2-(4-amino-3-iodophenyl)acetate

Participants

Reaction Steps

To a cooled solution (5° C.) of (4-aminophenyl)acetic acid ethyl ester (25 g, 0.39 mol) in CH2Cl2 (150 mL) is added triethylamine (14.1 g, 0.139 mmol) followed by a solution of iodine monochloride (21.5 g, 0.132 mol) in CH2Cl2 (100 mL). Cooling is removed and the reaction mixture is stirred for 4 hours at room temperature. The solution is concentrated in vacuo and chromatographed with a gradient of hexane/ethyl acetate (5%-30%) within 1 hour to give the desired product (19.5 g, 46%). MS: 305.9 (M+1)+.

Provenance & Evidence