反応 #577040

反応方程式

diethyl(3-pyridyl)borane

methyl-3-iodobenzoate

potassium phosphate

→

methyl-3-(pyridin-3-yl)benzoate

収率 68.1%

溶媒

DMF

water

反応条件

後処理

1. 1
   温度was heated at 80 degrees under argon
2. 2
   抽出extracted with ethyl acetate
3. 3
   ろ過The organic layer was filtered
4. 4
   洗浄washed with water
5. 5
   workup.ADDITIONTo the organic fraction was added
6. 6
   濃縮concentrated HCL (65 ml)
7. 7
   その他The organic layer was separated
8. 8
   抽出extracted with aqueous HCl
9. 9
   抽出The combined acid extractions
10. 10
    workup.ADDITIONwere treated with ethyl acetate
11. 11
    その他The organic layer was separated
12. 12
    洗浄washed with water and saturated sodium bicarbonate solution
13. 13
    乾燥dried over sodium sulfate
14. 14
    ろ過The solution was filtered
15. 15
    濃縮concentrated

実験手順

A mixture of diethyl(3-pyridyl)borane (176.4 g, 1.2 mole), 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).

出典