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

2-iodo-3-(4fluorophenylmethyl)thiophene

methylmagnesium bromide

→

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

수율 48.0%

용매

ether

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후처리

1. 1
   기타The reaction mixture was quenched with saturated aqueous NH4Cl
2. 2
   추출extracted with ethyl acetate
3. 3
   세척The organic phase was washed with 1N aqueous H3PO4, saturated aqueous NaHCO3, saturated aqueous Na2S2O3, and brine
4. 4
   건조dried over MgSO4
5. 5
   여과filtered
6. 6
   농축concentrated in vacuo

실험 절차

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%).

출처