Methanesulfonyl chloride → 3-Bromo-5-(prop-1-en-2-yl)pyridine

To a solution of 2-(5-bromo-pyridin-3-yl)-propan-2-ol, prepared as described in Example 16a (200 mg, 0.93 mmol) in dichloromethane (8 mL) at 0° C. was added diisopropylethylamine (0.63 mL 3.7 mmol) followed by methanesulfonyl chloride (0.14 mL, 1.85 mmol). After 5 minutes the reaction was place at room temperature and stirred for an additional half hour. The reaction was quenched with saturated aqueous sodium bicarbonate, diluted with brine and ethyl acetate and the layers were separated. The aqueous layer was extracted two additional times with ethyl acetate, and the organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated. The resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, 0 to 50%) to furnish 3-bromo-5-isopropenyl-pyridine; MS: (ES+) m/z 198.0 (M+H)+.

1. customThe reaction was quenched with saturated aqueous sodium bicarbonate
2. additiondiluted with brine and ethyl acetate
3. customthe layers were separated
4. extractionThe aqueous layer was extracted two additional times with ethyl acetate
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customThe resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, 0 to 50%)

ORD record

ord-c601d62cb9cb4775bde9f1949b628b03

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778972B2