3,7-Dimethyl-1-octanol → 1-Bromo-3,7-dimethyloctane

Participants

Reaction Conditions

Reaction Steps

To a solution of 3,7-dimethyl-1-octanol (50.0 ml, 0.264 mol) and triphenylphosphine (86.9 g, 0.331 mol) in 300 ml of CH2Cl2 were added N-bromosuccinimide (56.6 g, 0.318 mol) in portions at 0° C. After stirring at 0° C. for 2 h, the solvent was evaporated. The residue was treated with hexane and filtered. The solids were washed thoroughly with hexane and the combined hexane extracts evaporated. The residue was chromatographed on silica gel with hexane. Yield=54.13 g (93% based on 50.0 ml of 3,7-dimethyl-1-octanol). 1H NMR (360 MHz, CDCl3): δ 3.37-3.50 (m, 2H, —CH2Br), 1.07-1.94 (m, 10H, (CH3)2CHCH2CH2CH2CH(CH3)CH2CH2Br), 0.89 (d, 3H, J=6.5 Hz, —CH3), 0.87 (d, 6H, J=6.8 Hz, —CH3). CI MS m/z: 220.048 (M+) (calcd 220.083).

Provenance & Evidence