1,5-Dibromopentane → (5-Bromopentyl)cyclohexane

Participants

Reaction Conditions

Reaction Steps

A mixture of 1,5-dibromopentane (16 gm, 69.97 mmol) in THF (20 ml) and a solution of (Li2CuCl4 in ether, 14 ml) under nitrogen at 5-10° C. was stirred for 25 minutes and then cyclohexyl magnesium bromide (10 gm, 69.97 mmol) was added dropwise over 30 minutes. The reaction was stirred at 0° C. for another 1 h, then at room temperature for 12 hr. The reaction mixture was cooled to 0° C., saturated with NH4Cl solution (20 ml), diluted with ethyl acetate (100 ml) and the combined organic layer was separated, washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the crude product was purified by column chromatography using hexane as an eluent. The pure product was an oily liquid (12.84 gm). 1H NMR (CDCl3): 0.8 (t, 2H, J=10.2 Hz), 1.00-1.38 (m, 9H), 1.52-168 (m, 6H), 1.70-1.80 (m, 2H), 3.38 (t, 2H, J=7.2 Hz).

Provenance & Evidence