Dimethyl Sulfoxide → 2-Acetyl-6-bromopyridine

Temperature

-60 °C

Oxalyl chloride (2.1 mL, 3.81 mmol) in dry CH2Cl2 was cooled to −70° C. followed by adding DMSO (0.6 mL, 8.39 mmol) dropwise. After stirred for 5 min under −60° C., 1-(6-bromo-pyridin-2-yl)-ethanol (770 mg, 3.81 mmol) in dry CH2CL2 (10 mL) was added dropwise. After stirred for 30 min, TEA (2.7 mL, 19.83 mmol) was added and the resulting mixture was warmed to RT and stirred for 1 h. The reaction mixture was quenched with H2O. The organic layer was washed with H2O, brine, and dried over MgSO4. Solvent was removed and the crude compound was purified by chromatography on silica gel. Elution with hexane:acetone mixture (90:10) gave a white solid. MS m/z: 200.3(M+H). Calc'd. for C7H8BrNO-198.96.

1. stirringAfter stirred for 30 min
2. temperaturethe resulting mixture was warmed to RT
3. stirringstirred for 1 h
4. customThe reaction mixture was quenched with H2O
5. washThe organic layer was washed with H2O, brine
6. dry with materialdried over MgSO4
7. customSolvent was removed
8. customthe crude compound was purified by chromatography on silica gel
9. washElution with hexane
10. customacetone mixture (90:10) gave a white solid

ORD record

ord-c21aa86c42e04ba98ae77c7434553497

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07196104B2