Benzoyl Peroxide → 2-Bromomethyl-5-nitro-benzenesulfonic Acid, 2,2-Dimethylpropyl Ester

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Reaction Steps

To a solution of 2-methyl-5-nitro-benzenesulfonic acid, 2,2-dimethylpropyl ester, Example 24 (1.0 g, 3.48 mmol) in dry carbon tetrachloride (50 mL) was added 126 mg (0.52 mmol) of benzoyl peroxide and 712 mg (4.0 mmol) of recrystallized N-bromosuccinimide. A reflux condensor was attached and the mixture was heated to reflux and stirred overnight. After cooling to room temperature the reaction mixture was diluted with ethyl acetate (250 mL) and washed with water, followed by saturated sodium bicarbonate, and then brine. The organic layer was dried (MgSO4) and concentrated to dryness on a rotary evaporator. Purification by flash column chromatography using 10% ethyl acetate in hexanes gave 560 mg (44%) of the title compound as a white solid: 1HNMR (CDCl3): d 8.83 (d, J=2 Hz, 1H), 8.48 (dd, J=2 Hz, 9 Hz, 1H), 7.92 (d, J=9 Hz, 1H), 4.96 (s, 2H), 3.85 (s, 2H), 1.0 (s, 9H); MS (ES-NEG): [M−H] 364/366; Anal. Calc. for C12H16BrNO5S: C, 39.35; H, 4.40; N, 3.82. Found: C, 39.88; H, 4.16; N, 3.85.

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