4-Iodotoluene → 4-Iodobenzyl bromide

Participants

Reaction Steps

A mixture of 4-iodotoluene (21.8 g, 100 mmol), N-bromosuccinimide (18.69 g, 105 mmol) and αα-azobisisobutyronitrile (100 mg) in carbon tetrachloride (100 ml) was refluxed for 20 hours. The reaction was cooled, the precipitate filtered, washed with carbon tetrachloride (50 ml), and the filtrate evaporated. The residue was chromatographed on silica, eluting with petrol (60°-80° C.) to give the product as a white solid (13 g, 45%); δH (CDCl3) 4.42 (2H, ArCH2Br), 7.11 (2H, d, J 15.3 Hz, 2-H, 6-H), 7.67 (2H, d, J 15.3 Hz, 3'-H, 5'-H).

Provenance & Evidence