Dimethyl Sulfoxide → 9-Bromononanal

Temperature

-15 °C

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.

1. additionsulfur trioxide-pyridine complex (21.4 g) was added in 4 portions at 5 min intervals
2. additionafter completion of the addition
3. customthe layers were separated
4. washThe organic layer was washed with 1M aqueous sodium bisulfate solution (4×250 mL), saturated aqueous potassium carbonate (250 mL) and brine (2×200 mL)
5. dry with materialdried over sodium sulphate
6. filtrationfiltered
7. customevaporated in vacuo

ORD record

ord-b3621bea3dde4054a5809b98caaafe4c

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629271B2