Bromination of an electron-rich aromatic ring (3,5-dimethylanisole); 4-bromo-3,5-dimethylanisole

Mark Birri (mark_birri@hotmail.com),
A contribution from the Caddick Group, Sussex

Chemicals Used
3,5-dimethylanisole (Avocado), Bromine (Aldrich), Carbon Tetrachloride (Bulk).

Procedure
To a solution of 3,5-dimethylanisole (26mL, 183.8mmol) in CCl₄ (300mL), cooled to 0^oC was added a solution of bromine (9.4mL, 183.8mmol) in CCl₄ (150mL) over three hours by the aid of an addition funnel. The reaction mixture was stirred for a further 1/2 h at 0^oC. The resulting orange/brown solution was quenched by addition of 3% NaOH solution (500mL). The organic layer was isolated and dried over MgSO₄, filtered and concentrated in vacuo to yield a slightly yellow oil (39.5g, 100%).

Author's Comments
The reaction worked well producing only mono-brominated product. Nmr analysis showed the compound to be of sufficiant purity for use without further purification, although it is possible to purify this oil by distillation. Although I myself have only carried out this reaction once, it has been used for the synthesis of the neocarzinostatin naphthoate synthesis numerous times within the group.

Data
1H nmr (300MHz, CDCl₃) 2.40 (6H, s), 3.77 (3H, s), 6.66 (2H, s).

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

Other References

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