N-bromobutanimide → 6-(Bromomethyl)-1,1,4,4-Tetramethyl-1,2,3,4-Tetrahydronaphthalene

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Reaction Conditions

Reaction Steps

A solution of 1,2,3,4-tetrahydro-1,1,4,4,6-pentamethylnaphthalene 1 (2.00 g, 9.88 mmol), N-bromosuccinimide (1.85 mmol, 10.37 mmol), benzoyl peroxide (91 mg, 0.28 mmol) in 35 mL of CCl4 was heated at reflux (84° C., oil bath) for 2.5 h. After cooling top room temperature, the solution was concentrated in vacuo. Diethyl ether (100 mL) was added and the solution was filtered (to remove the succinimide formed) and concentrated to give a crude oil. The crude oil was purified by silica gel column chromatography using as eluent petroleum ether. 6-(Bromomethyl)-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene 8 (2.01 g, 72.5% yield) was obtained as a colourless oil.

Provenance & Evidence