Ammonium Chloride → 2-Methyl-4-phenylthiophene

HRID 853111Notes

Reaction equation

HRID 853111 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:10]1[CH:11]=[C:12]([CH3:15])[S:13][CH:14]=1.[NH4+].[Cl-]>CCOCC>[CH3:15][C:12]1[S:13][CH:14]=[C:10]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:11]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 6385844-Bromo-2-methylthiopheneHCID 178418255HCID 178418255, compound

Product 1

HCID 114010612-Methyl-4-phenylthiophene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of PhMgBr (prepared from 1.65 g of Mg (0.0678 mol) and 10.64 g of PhBr (0.0678 mol) in 40 mL of diethyl ether) was added to a mixture of 10 g (0.0565 mol) of 4-bromo-2-methylthiophene and 0.62 g (0.0012 mol) of NiCl2dppp in 50 mL of ether under stirring at reflux. The reaction mixture was refluxed for additional 3 h and then stirred overnight. The resulting mixture was treated with 10% aqueous NH4Cl, the organic layer was separated, washed with 10% aqueous NH4Cl and then dried with anhydrous Na2SO4. Solvent was evaporated, the residue was recrystallized from methanol. Yield 6.8 g (70%) of colorless crystals.

Workup

  1. temperatureat reflux
  2. temperatureThe reaction mixture was refluxed for additional 3 h
  3. stirringstirred overnight
  4. customthe organic layer was separated
  5. washwashed with 10% aqueous NH4Cl
  6. dry with materialdried with anhydrous Na2SO4
  7. customSolvent was evaporated
  8. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-c307529e2a6f4798bb27b1ebd18a19fe
Source dataset
uspto-grants-2007_08
Patent number
US07253292B2

Reaction notes

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