반응 #320662

반응 방정식

2-bromo-3-hydroxypyridine

phenylboronic acid

HCl

→

3-hydroxy-2-phenylpyridine

수율 45.4%

용매

toluene

ethanol

sodium hydroxide

water

반응 조건

후처리

1. 1
   기타was degassed with a stream of nitrogen
2. 2
   workup.ADDITIONThe mixture was diluted with water (50 mL) and ethyl acetate (100 mL)
3. 3
   건조the organic layer was dried over sodium sulfate
4. 4
   농축concentrated
5. 5
   기타affording a yellow solid
6. 6
   추출the resulting solution was extracted with ethyl acetate
7. 7
   추출again was extracted with ethyl acetate
8. 8
   건조The combined organic extracts were dried with sodium sulfate
9. 9
   농축concentrated to an oily solid, which
10. 10
    기타was triturated with 2:1 hexane/ethylacetate

실험 절차

A mixture of 2-bromo-3-hydroxypyridine (2.20 g, 12.6 mmol), phenylboronic acid (2.00 g, 16.3 mmol) and palladium (tetrakis)triphenylphosphine (250 mg) in toluene (30 mL), ethanol (15 mL) and 5% aqueous sodium hydroxide (15 mL) was degassed with a stream of nitrogen and stirred vigorously at 100° C. overnight. The mixture was diluted with water (50 mL) and ethyl acetate (100 mL), and the organic layer was dried over sodium sulfate and concentrated, affording a yellow solid. This material was suspended in water (100 mL), a few mL of 1N HCl was added, and the resulting solution was extracted with ethyl acetate. The aqueous layer was neutralized with saturated aqueous sodium bicarbonate, and again was extracted with ethyl acetate. The combined organic extracts were dried with sodium sulfate and concentrated to an oily solid, which was triturated with 2:1 hexane/ethylacetate, affording 0.98 g of 3-hydroxy-2-phenylpyridine.

출처