Hydrochloric Acid → 2-Bromo-4-isopropylaniline

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A mixture of 99 g (0.73 mol) of 4-isopropylaniline (Acros) and 300 ml of acetic acid was refluxed for 1 h; then, 75 g of acetic anhydride was added dropwise while vigorously stirring. The resulting solution was cooled to 50° C., and 37.4 ml of bromine was added dropwise, while vigorously stirring, over ca. 30 min. Then, 370 ml of 12 M HCl was added and this mixture was refluxed until a precipitate was formed. This precipitate was separated, washed with 2×150 ml of methyl-tert-butyl ether, and dried in vacuum. A mixture of the solid obtained and a solution of 112 g of KOH in 300 ml of water was stirred at 50-60° C. for 1 h. The organic layer was separated, and the aqueous layer was extracted with 2×150 ml of methyl-tert-butyl ether. The combined extract was dried over K2CO3 and evaporated to dryness. Fractional distillation gave the title product, b.p. 107-111° C./3 mm Hg. Yield 83.7 g (77%) of yellowish oil.

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