Iodine → 5-Chloro-2-iodo-4-methylaniline

Participants

Reaction Steps

A solution of iodine (9.86 g; 38.84 mmol) and potassium iodide (6.45 g; 38.84 mmol) in water was added dropwise to a suspension of 3-chloro-4-methylaniline (5.00 g; 35.31 g) in a solution of sodium bicarbonate (4.75 g; 56.50 mmol). The resulting mixture was stirred for 72 hours at room temperature and filtered. The solid was dissolved in dichloromethane, washed with a saturated solution of sodium thiosulfate, and the organic layer was dried and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane) to yield 2.30 g (24%) of the title compound as a brown solid.

Provenance & Evidence