Dimethyl Sulfoxide → 9-Bromononanal

Participants

Reaction Conditions

Reaction Steps

N-Ethyldiisopropylamine (23 mL) and DMSO (9.7 mL) were added to a solution of 9-bromo-1-nonanol (10.0 g) in dry DCM (230 mL) at RT under argon. The mixture was cooled to −15° C. and sulfur trioxide-pyridine complex (21.4 g) was added in 4 portions at 5 min intervals. The mixture was stirred for 15 min after completion of the addition then water (200 mL) was added and the layers were separated. The organic layer was washed with 1M aqueous sodium bisulfate solution (4×250 mL), saturated aqueous potassium carbonate (250 mL) and brine (2×200 mL), dried over sodium sulphate, filtered and evaporated in vacuo to give the subtitled compound as an orange oil. Yield 9.02 g.

Provenance & Evidence