3-Chloro-4-fluoroaniline → 5-Chloro-4-fluoro-2-iodobenzenamine

Participants

Reaction Steps

A mixture of 3-chloro-4-fluoroaniline (12.9 g, 88.9 mmol) and NIS (22.0 g, 97.8 mmol) in AcOH (90 mL) is stirred at RT for 1.5 h. After completion, the reaction mixture is quenched by H2O, DCM is added and the organic layer is washed with brine, dried over MgSO4 and evaporated in vacuo. Silica gel flash chromatography of the residue affords 5-chloro-4-fluoro-2-iodoaniline as a colorless powder; HPLC: AtRet=4.75 min; 1HNMR (CDCl3) 7.40 (d, 1H), 6.75 (d, 1H), 4.00 (bs, 2H).

Provenance & Evidence