4-Methylbenzophenone → 4-(Bromomethyl)benzophenone

Participants

Reaction Steps

A stirred mixture of 4-methylbenzophenone (15.02 g, 76.6 mmol) and N-bromosuccinimide (14.2 g, 79.8 mmol) in CHCl3 (100 cm3) was heated under gentle reflux for 18 h with a 100 W bulb shining 2 cm from the flask. The reaction mixture was washed with water, dried (MgSO4) and solvent was removed in vacuo). The resulting solid was then washed with Et2O to remove any starting material to leave the product as a white solid (15.07 g, 71.5%, mp 110–112° C. (lit. 110–111°); δH (200 MHz; CDCl3) 4.55 (2 H, s, CH2Br), 7.46–7.70 (5 H, m, ArH), 7.80–7.9 (4 H, m, ArH o- to C═O); m/z 277 ([M81Br+H]+, 25%) and 275 ([M79Br+H]−, 25%), 197 (100%).

Provenance & Evidence