Carbon tetrabromide → HCID 18988240, compound

Participants

Reaction Conditions

Reaction Steps

Part E. The alcohol compound from Part D above (3.39 g, 13.4 mmol) and carbon tetrabromide (5.78 g, 17.4 mmol) were dissolved in methylene chloride (30 mL). This solution was cooled to 0° C. and treated with a 20 mL methylene chloride solution of triphenylphosphine (4.57 g, 17.4 mmol). The solution was allowed to stir for 14 hours, then evaporated. The residual oil was separated by flash chromatography (1:9 ethyl acetate-hexane) to afford the product, 1-bromo-2-(3,4-dimethoxybenzyl)hexane, as an oil (4.01 g, 12.7 mmol, 95%). 1H NMR (CDCl3): δ 6.81-6.71 (3H, m); 3.88 (3H, s); 3.87 (3H, s); 3.41 (1H, dd, J=9.9, 4,4 Hz); 3.33 (1H, dd, J=9.9, 4.0 Hz); 2.64 (1H, dd, J=13.5, 6.2 Hz); 2.58 (1H, dd, J=13.5, 8.0 Hz); 1.90-1.80 (1H, m); 1.48-1.24 (6H, m); 0.91 (3H, t, J=6.8 Hz). Mass spectrum (NH3 -CI/DDIP): m/z 334 (98%); 332 (100%); 317 (33%); 315 (34%); 252 (3%).

Provenance & Evidence