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

HRID 52189Notes

Reaction equation

HRID 52189 reaction equation
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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418745HCID 178418745, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-b9357db81ccf486c92cf642395755be2
Source dataset
uspto-grants-1997_04
Patent number
US05616596

Reaction notes

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