Ethanol → 1-Bromo-3-isopropylbenzene

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To a mixture of 1000 ml of 96% ethanol and 94 ml of 98% H2SO4, 117 g (0.55 mol) of 2-bromo-4-isopropylaniline was added, while vigorously stirring, at −5° C. over 15 min. Then, a solution of 63 g of NaNO2 in 125 ml of water was added at this temperature over 1 h, and the resulting mixture was stirred for about 30 min longer. Then, 12 g of copper powder was added. The reaction mixture was refluxed for 4 h and then filtered through a glass frit (G3). The filtrate was poured into 2500 cm3 of cold water. The organic product was extracted with 4×400 ml of dichloromethane. The combined extract was dried over K2CO3 and evaporated to dryness. Fractional distillation gave the title product, b.p. 64-67° C./3 mm Hg. Yield 117.4 g (75%) of yellowish oil.

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