Bromine → 3-Bromo-2-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene

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A solution of 2-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene (from Example 2.1, 12.1 g) in 80 ml of carbon tetrachloride, containing 327 mg of pulverised iron powder, was cooled to 0° C. and treated dropwise with a solution of 7.84 g of Br2 in 8 ml of carbon tetrachloride. The mixture was stirred at 0° C. for 4 hours. The reaction mixture was filtered and then poured into 200 ml ice/water. Extraction of the biphasic mixture with 3 portions of 100 ml of methylene chloride was followed by a washing of the combined organic extracts with 100 ml of saturated aqueous sodium bicarbonate solution and 100 ml water. The organic phase was dried over MgSO4 and concentrated in vacuo, giving a yellow oil. The crude product was distilled under vacuum, yielding 14 g of a pale yellow oil. B.p. 148° C. at 0.09 bar.

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