反应详情

A mixture of diethyl(3-pyridyl)borane (176.4 g, 1.2mole), methyl-3-iodobenzoate(262 g, 1 mole), potassium phosphate (318.4 g, 1.5 mole) and tetrakistriphenlyphosphine palladium (0) (57.8 g, 0.05 mole) in DMF (1000 ml) was heated at 80 degrees under argon. After 10 h, the mixture was diluted with water and extracted with ethyl acetate. The organic layer was filtered and washed with water. To the organic fraction was added concentrated HCL (65 ml). The organic layer was separated and extracted with aqueous HCl. The combined acid extractions were treated with ethyl acetate, followed by 50% aqueous sodium hydroxide (55 ml). The organic layer was separated, washed with water and saturated sodium bicarbonate solution, then dried over sodium sulfate. The solution was filtered and concentrated to give methyl-3-(pyridin-3-yl)benzoate (145.3 g).

1. temperaturewas heated at 80 degrees under argon
2. extractionextracted with ethyl acetate
3. filtrationThe organic layer was filtered
4. washwashed with water
5. additionTo the organic fraction was added
6. concentrationconcentrated HCL (65 ml)
7. customThe organic layer was separated
8. extractionextracted with aqueous HCl
9. extractionThe combined acid extractions
10. additionwere treated with ethyl acetate
11. customThe organic layer was separated
12. washwashed with water and saturated sodium bicarbonate solution
13. dry with materialdried over sodium sulfate
14. filtrationThe solution was filtered
15. concentrationconcentrated