반응 #80451

반응 방정식

thiophene

4-fluorobenzyl bromide

n-butyllithium

hexane

→

2-(4-fluorophenylmethyl)thiophene

수율 81.0%

용매

THF

ether

THF

반응 조건

후처리

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

실험 절차

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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