2-Bromopropane → 3-Bromo-2-isopropoxy-5-(trifluoromethyl)pyridine

Temperature

50 °C

2-Bromopropane (0.78 ml, 8.3 mmol) was added to a stirred suspension of 3-bromo-5-trifluoromethyl-2(1H)-pyridone (2.0 g, 8.3 mmol) and silver carbonate (1.16 g, 4.2 mmol) in hexane (40 ml) and the mixture stirred at 50° C. for 14 h, then at reflux for 3 h. More 2-bromopropane (0.78 ml) was added and reflux resumed for a further 3 h. On cooling, the mixture was filtered, the filtrate diluted with hexane (100 ml) and washed with water (50 ml). The organic layer was dried (Na2SO4), evaporated, and the residual oil subjected to column chromatography over silica gel, eluting with ethyl acetate/hexane (5:95) to leave the product as a colourless oil (1.68 g).

1. temperatureat reflux for 3 h
2. temperaturereflux
3. waitresumed for a further 3 h
4. temperatureOn cooling
5. filtrationthe mixture was filtered
6. additionthe filtrate diluted with hexane (100 ml)
7. washwashed with water (50 ml)
8. dry with materialThe organic layer was dried (Na2SO4)
9. customevaporated
10. washeluting with ethyl acetate/hexane (5:95)

ORD record

ord-3ac287898c6343baa3774352a195dfe6

Source dataset

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06225320B1