4-bromo-3,5-dimethylanisole (see Synthetic Page X),
N-Bromosuccinimide (NBS) (Avocado, recrystallised),
Benzyl peroxide (Aldrich),
Carbon tetrachloride.

A solution under N₂ of 4-bromo-3,5-dimethylanisole (39.5g, 183.8mmol), N-bromosuccinimide (32.7g, 183.8mmol), benzyl peroxide (2.23g, 9.19mmol) in CCl₄ was heated at reflux at 80^oC for 3h. After cooling to r.t, the light yellow solution filtered and concentrated to give an orange oil which precipitated a yellow/white solid. Recrystallisation from 9:1 hexane/ethyl acetate yielded white crystals of 3-bromomethyl-4-bromo-5-methylanisole (17.5g, 32.4%).

A simple and effective reaction, however I am unsure about the percentage yield. This reaction has been carried out on this scale by other members of the group, usually yielding around 25g of product i.e. 50% yield.

1H nmr (300MHz, CDCl₃) 2.41 (3H, s), 3.80 (3H, s), 4.61 (2H, s), 6.77 (1H, d, J=3Hz), 6.86 (1H, d, J=3Hz)

Rucker, M. Brueckner, R. Synlett, 1997, 1187-1189