反应 #320662

反应方程式

2-bromo-3-hydroxypyridine

phenylboronic acid

HCl

→

3-hydroxy-2-phenylpyridine

收率 45.4%

溶剂

toluene

ethanol

sodium hydroxide

water

反应条件

后处理

1. 1
   其他was degassed with a stream of nitrogen
2. 2
   workup.ADDITIONThe mixture was diluted with water (50 mL) and ethyl acetate (100 mL)
3. 3
   干燥the organic layer was dried over sodium sulfate
4. 4
   浓缩concentrated
5. 5
   其他affording a yellow solid
6. 6
   萃取the resulting solution was extracted with ethyl acetate
7. 7
   萃取again was extracted with ethyl acetate
8. 8
   干燥The combined organic extracts were dried with sodium sulfate
9. 9
   浓缩concentrated to an oily solid, which
10. 10
    其他was triturated with 2:1 hexane/ethylacetate

实验过程

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.

来源