3,5-Dichloroaniline → 3,5-Dichloro-2-iodoaniline

Participants

Reaction Steps

Dissolve 3,5-dichloroaniline (10g, 61.5mmol) in 1:1 acetic acid/methylene chloride (200mL). Add N-iodosuccinimide (16.9g, 61.5mmol) as a solid and stir at room temperature in the absence of light for 8 hours. Pour the solution into saturated sodium hydrogen carbonate (200mL) and extract into methylene chloride (100mL). Wash with saturated sodium hydrogen carbonate (200mL), dry (MgSO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography to give the title compound (8.1g, 45%); mp 61°-63° C.

Provenance & Evidence