反应 #80451

反应方程式

thiophene

4-fluorobenzyl bromide

n-butyllithium

hexane

→

2-(4-fluorophenylmethyl)thiophene

收率 81.0%

溶剂

THF

ether

THF

反应条件

后处理

1. 1
   其他transferred by cannula into a -78° C.
2. 2
   workup.STIRRINGThe reaction mixture was stirred at ambient temperature under nitrogen overnight
3. 3
   其他quenched with saturated NH4Cl solution (100 mL)
4. 4
   其他partitioned between ether and additional NH4Cl solution
5. 5
   干燥The ether layer was dried over MgSO4
6. 6
   浓缩concentrated in vacuo
7. 7
   workup.DISTILLATIONthe residue subjected to vacuum distillation

实验过程

A solution of thiophene (12.6 g, 0.15 mol) in a mixture of anhydrous ether (230 mL) and anhydrous THF (70 mL) was treated dropwise at 0° C. with a 2.5M solution of n-butyllithium in hexane (54.0 mL, 0.134 mol). The mixture was stirred at 0° C. for 1.5 hours and then transferred by cannula into a -78° C. solution of 4-fluorobenzyl bromide (23.6 g, 0.125 mol) containing tetrakis(triphenylphosphine) palladium(0) (1.25 g) in anhydrous THF (200 mL). The reaction mixture was stirred at ambient temperature under nitrogen overnight and then quenched with saturated NH4Cl solution (100 mL) and partitioned between ether and additional NH4Cl solution. The ether layer was dried over MgSO4, concentrated in vacuo and the residue subjected to vacuum distillation to give 19.4 g (81% ) of 2-(4-fluorophenylmethyl)thiophene. b.p. 74°-83° C. at 0.6-0.7 mm of Hg.

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