Tributylvinyltin → 5-Ethenyl-2-(trifluoromethyl)pyridine

Temperature

100 °C

2 g of 5-bromo-2-(trifluoromethyl)pyridine was dissolved in DMF:THF (3:1, 12 mL). vinyltributyltin (3 g) and tetrakis (triphenylphosphine)palladium (135 mg) were added to this solution. The reaction mixture was degassed and purged with nitrogen for 5 min and then heated at 100° C. for 2 h. at which point the reaction was found complete (monitored by TLC). The reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure (Caution: product may be volatile) and the residue was purified by SiO2 chromatography (100-200 mesh, eluent: hexane-ethyl acetate gradient). The requisite fractions were concentrated below 40° C. under reduced pressure to obtain 20.3 g of 2-(trifluoromethyl)-5-vinylpyridine as oil.

1. customThe reaction mixture was degassed
2. custompurged with nitrogen for 5 min
3. additionThe reaction mixture was diluted with water
4. extractionextracted with ethyl acetate
5. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
6. customevaporated under reduced pressure (Caution: product may be volatile)
7. customthe residue was purified by SiO2 chromatography (100-200 mesh, eluent: hexane-ethyl acetate gradient)
8. concentrationThe requisite fractions were concentrated below 40° C. under reduced pressure

ORD record

ord-cc9191cf6c6440d7a2aa3366d0dd9581

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08999978B2