Benzoyl Peroxide → 2-Bromo-1-(bromomethyl)-4-tert-butylbenzene

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Reaction Steps

To a mixture of 227 g (1.00 mol) of 2-bromo-4-tert-butyl-1-methylbenzene, 160 g (1.00 mol) of bromine and 1.4 liter of CCl4 1.0 g of benzoyl peroxide was added. This mixture was refluxed until evolution of hydrogen bomide was stopped, and red color of bromine disappeared. The resulting mixture was evaporated using rotary evaporated. Fractional rectification of the residue gave 273 g (89%) of the title product, b.p. 138° C.-141° C./4 mm Hg. Anal. calc. for C11H14Br2: C, 43.17; H, 4.61. Found: C, 43.30; H, 6.72. 1H NMR (CDCl3): δ 7.56 (d, J=1.8 Hz, 3-H), 7.37 (d, J=8.1 Hz, 1H, 5-H), 7.30 (dd, J=8.1 Hz, J=1.8 Hz, 1H, 6-H), 4.59 (s, 2H, CH2Br), 1.29 (s, 9H, tBu). 13C{1H} NMR (CDCl3): δ 153.9, 133.9, 130.9, 130.4, 125.1, 124.4, 34.7, 33.4, 31.06.

Provenance & Evidence