Bromobenzene → 6-Bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene

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Reaction Steps

Aluminum chloride (700 mg, 5.25 mmol) was added slowly to a solution of 2,5-dichloro-2,5-dimethylhexane (11 g, 60 mmol) in bromobenzene (90 mL) at 0° C. After stirred for 20 min, the mixture was diluted with 100 mL of ether:hexane (1:1), washed with ice-water (1×10 mL), 10% HCl (1×10 mL) and brine (1×10 mL), dried (MgSO4) and concentrated to afford a brown oil. The crude was then distilled using Coughler distillation to yield the title compound (13.2 g, 83% yield) as a white solid:

Provenance & Evidence