Isopropanol → 2-Bromo-6-isopropoxypyridine

Temperature

80 °C

Sodium (0.50 g, 21.7 mmol) was dissolved in isopropanol (50 ml) under an atmosphere of nitrogen with warming at 80° C., then allowed to cool to ambient temperature. 2,6-Dibromopyridine (10.0 g, 41.4 mmol) was added and the solution heated to 90° C. After 5 h the cooled reaction mixture was partitioned between diethyl ether (150 ml) and water (100 ml). Diethyl ether extracts were washed with water and saturated brine then dried over magnesium sulphate, filtered and evaporated in vacuo to give a semi-solid. Addition of isohexane, filtration and concentration in vacuo gave a residue that was purified by chromatography on silica gel eluting with dichloromethane to give 2-bromo-6-isopropoxypyridine (2.1 g) as a colourless liquid: δH (400 MHz, CDCl3) 1.33 (6H, d, J 6), 5.28 (1H, quin, J 6), 6.60 (1H, d, J 8), 7.00 (1H, d, J 7), 7.38 (1H, dd, J 7 and 8); m/z (ES+) 214/216 (M++H).

1. temperatureto cool to ambient temperature
2. temperaturethe solution heated to 90° C
3. customAfter 5 h the cooled reaction mixture
4. customwas partitioned between diethyl ether (150 ml) and water (100 ml)
5. washDiethyl ether extracts were washed with water and saturated brine
6. dry with materialthen dried over magnesium sulphate
7. filtrationfiltered
8. customevaporated in vacuo
9. customto give a semi-solid
10. customgave a residue that
11. customwas purified by chromatography on silica gel eluting with dichloromethane

ORD record

ord-004fc8d0930a4d4b9835e725f6d594e5

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07030128B2