N-bromobutanimide → 2-Bromo-1-(bromomethyl)-4-chlorobenzene

Participants

Reaction Steps

To a 500 ml 3-necked pyrex round bottomed flask equipped with a magnetic stirring bar, reflux condenser and argon inlet was added 2-bromo-4-chlorotoluene (10.00 g, 48.67 mmol), N-bromosuccinimide (18.66 g, 48.67 mmol) and dry, degassed carbon tetrachloride (200 ml). The stirred mixture was heated at reflux while being irradiated at a distance 10 cm by a 150 watt Hanovia low pressure mercury Lamp for 4 hours. The cooled reaction mixture was diluted with carbon tetrachloride and washed with water (2×200 ml) and brine (400 ml). Drying (MgSO4), filtration, and removal of the solvent in vacuo left compound (2a) as a colorless oil. HPLC analysis indicates the material to be approximately 80% of the monobromo and 20% of the dibromo material. 'H NMR (CDCl3) δ4.55 (s, 2H), 7.00-7.65 (m, 3H).

Provenance & Evidence