반응 #581366

반응 방정식

2-bromo-6-methylpyridine

sodium carbonate

4-carboxybenzeneboronic acid

→

title compound

수율 77.0%

4-(6-Methyl-2-pyridyl)benzoic acid

수율 77.0%

용매

DME

water

반응 조건

후처리

1. 1
   기타To a stirred, degassed
2. 2
   온도the mixture heated
3. 3
   온도to reflux for 18 h
4. 4
   온도On cooling
5. 5
   기타˜50% of the solvent was removed in vacuo
6. 6
   세척the residual aqueous solution was washed with EtOAc
7. 7
   세척washed with further EtOAc
8. 8
   workup.ADDITIONThe aqueous was then adjusted to pH 5 by addition of potassium carbonate causing formation of a white precipitate which
9. 9
   여과was collected by filtration
10. 10
    세척washed with water
11. 11
    기타dried

실험 절차

To a stirred, degassed mixture of 2-bromo-6-methylpyridine (3 g, 17 mmol), sodium carbonate (10.8 g, 100 mmol) and 4-carboxybenzeneboronic acid (2.3 g, 14 mmol) in DME (150 ml) and water (150 ml) under an argon atmosphere was added tetrakis(triphenylphosphine) palladium (0) (350 mg) and the mixture heated to reflux for 18 h. On cooling, ˜50% of the solvent was removed in vacuo and the residual aqueous solution was washed with EtOAc, then acidified to pH1 with concentrated HCl and washed with further EtOAc. The aqueous was then adjusted to pH 5 by addition of potassium carbonate causing formation of a white precipitate which was collected by filtration, washed with water and dried to give the title compound as a white solid (2.3 g). MS (ES): MH+ 212.

출처