2-Iodo-3-(4fluorophenylmethyl)thiophene → 2-Methyl-3-(4-fluorophenylmethyl)thiophene

HRID 52189노트

반응식

HRID 52189 반응식
I[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1.[CH3:15][Mg]Br>CCOCC.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:15][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1

참가 물질

5

반응물 2

HCID 199632792-Iodo-3-(4fluorophenylmethyl)thiopheneHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 199632702-Methyl-3-(4-fluorophenylmethyl)thiophene수율 48%

시약·촉매·용매 2

HCID 178418745HCID 178418745, 화합물촉매HCID 3283Diethyl Ether용매

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%).

후처리

  1. customThe reaction mixture was quenched with saturated aqueous NH4Cl
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with 1N aqueous H3PO4, saturated aqueous NaHCO3, saturated aqueous Na2S2O3, and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-b9357db81ccf486c92cf642395755be2
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616596

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