Triethylamine → 2-Bromo-6-(prop-1-en-2-yl)pyridine

A solution of 2-(6-bromopyridin-2-yl)propan-2-ol (2.44 g, 11.29 mmol) and methansulfonic anhydride (5.90 g, 33.9 mmol) in dichloromethane (35 mL) was charged with triethylamine (6.26 ml, 45.2 mmol). After three hours, the reaction mixture was partitioned between ethyl acetate (50 mL) and saturated aqueous sodium bicarbonate (25 mL). The layers were separated and the organic layer was washed with saturated aqueous sodium bicarbonate (25 mL) and brine (2×25 mL), dried over sodium sulfate, filtered, and concentrated. The resulting yellow liquid was purified by silica gel chromatography (2-20% ethyl acetate/hexanes) to afford the title compound. 1H NMR (600 MHz, d6-DMSO): δ 7.70 (t, 1H), 7.61 (d, 1H), 7.49 (d, 1H), 5.89 (s, 1H), 5.33 (s, 1H), 2.06 (s, 3H).

1. customthe reaction mixture was partitioned between ethyl acetate (50 mL) and saturated aqueous sodium bicarbonate (25 mL)
2. customThe layers were separated
3. washthe organic layer was washed with saturated aqueous sodium bicarbonate (25 mL) and brine (2×25 mL)
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customThe resulting yellow liquid was purified by silica gel chromatography (2-20% ethyl acetate/hexanes)

ORD record

ord-a32bf28efac7453db74792b89a264713

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08278335B2