反应 #80467

反应方程式

2-iodo-3-(4-fluorophenylmethyl)thiophene

2-iodo-3-(4fluorophenylmethyl)thiophene

methylmagnesium bromide

→

2-methyl-3-(4-fluorophenylmethyl)thiophene

收率 48.0%

溶剂

ether

反应条件

后处理

1. 1
   其他The reaction mixture was quenched with saturated aqueous NH4Cl
2. 2
   萃取extracted with ethyl acetate
3. 3
   洗涤The organic phase was washed with 1N aqueous H3PO4, saturated aqueous NaHCO3, saturated aqueous Na2S2O3, and brine
4. 4
   干燥dried over MgSO4
5. 5
   过滤filtered
6. 6
   浓缩concentrated in vacuo

实验过程

The 2-iodo-3-(4-fluorophenylmethyl)thiophene prepared in step 1 was taken up in ether and methylmagnesium bromide (3.0M in ether, 2.42 mL, 7.26 mmol) and dichloro [1,3-bis(diphenylphosphino)propane]nickel(II) (164 mg, 0.302 mmol) were added and the reaction mixture was stirred for 17 hours at ambient temperature. The reaction mixture was quenched with saturated aqueous NH4Cl and extracted with ethyl acetate. The organic phase was washed with 1N aqueous H3PO4, saturated aqueous NaHCO3, saturated aqueous Na2S2O3, and brine, dried over MgSO4, filtered, and concentrated in vacuo. Chromatography on silica gel (10% ethyl acetate/hexane) gave 2-methyl-3-(4-fluorophenylmethyl)thiophene (602 mg, 48%).

来源