N-bromobutanimide → 2-(Bromomethyl)-1-nitro-3-(trifluoromethyl)benzene

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Reaction Steps

To a solution of 2-methyl-1-nitro-3-trifluoromethyl-benzene (5.0 g, 24.4 mmol) in CCl4 (300 mL) was added N-bromosuccinimide (4.35 g, 24.4 mmol) and benzoyl peroxide (0.11 g, 0.45 mmol). The mixture was heated to reflux and exposed to light (300 W) for 20 h. The mixture was cooled to room temperature, filtered and concentrated. Purification by column chromatography (EtOAc-hexanes) afforded 3.03 g (44%) of the benzyl bromide, a yellow oil. 1H NMR (400 MHz, CDCl3) δ 4.93 (s, 2 H), 7.63 (t, J=8.1 Hz, 1 H), 7.94 (d, J=7.8 Hz, 1 H), 8.06 (d, J=8.1 Hz, 1 H).

Provenance & Evidence