反应 #355781

反应方程式

2-chloro-4-(trifluoromethyl)pyridine

4-(methylthio)phenylboronic acid

sodium carbonate

→

title compound

收率 99.3%

2-[4-(methylthio)phenyl]-4-(trifluoromethyl)-pyridine

收率 99.3%

溶剂

1,2-dimethoxyethane

反应条件

后处理

1. 1
   温度After cooling
2. 2
   浓缩concentration in vacuo
3. 3
   其他the residue was partitioned between ethyl acetate (350 mL) and water (400 mL)
4. 4
   其他separated
5. 5
   萃取The aqueous layer was further extracted with ethyl acetate (2×150 mL)
6. 6
   干燥the combined organic layers were dried over sodium sulfate
7. 7
   浓缩concentrated in vacuo
8. 8
   过滤Filtration through a pad of silica gel (200 g)
9. 9
   洗涤eluting with a gradient of ethyl acetate in cyclohexane

实验过程

To a mixture of 2-chloro-4-(trifluoromethyl)pyridine (19.9 g, 0.11 mol), 4-(methylthio)phenylboronic acid (21.9 g, 0.13 mol), 1M aqueous sodium carbonate (180 mL) and 1,2-dimethoxyethane (270 mL) under an atmosphere of nitrogen was added palladium tetrakistriphenylphosphine (3.78 g, 3.3 mmol) and the reaction heated at 100° C. for 14 hours. After cooling and concentration in vacuo, the residue was partitioned between ethyl acetate (350 mL) and water (400 mL) and separated. The aqueous layer was further extracted with ethyl acetate (2×150 mL) and the combined organic layers were dried over sodium sulfate and concentrated in vacuo. Filtration through a pad of silica gel (200 g) eluting with a gradient of ethyl acetate in cyclohexane gave the title compound (29.4 g) LC retention time 3.62 mins, MS m/z 269 (MH+).

来源