4-Bromotoluene → 2-(4-Methylphenyl)thiophene

HRID 2306498Notes

Reaction equation

HRID 2306498 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[Mg].Br[C:11]1[S:12][CH:13]=[CH:14][CH:15]=1>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:5]1([CH3:8])[CH:6]=[CH:7][C:2]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)=[CH:3][CH:4]=1

Participants

7

Reactant 3

HCID 78054-BromotolueneHCID 138512-BromothiopheneHCID 5462224Magnesium

Product 1

HCID 41284662-(4-Methylphenyl)thiopheneYield 84.8%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

The corresponding Grignard compound is prepared from 16 g of 4-bromotoluene and 2.23 g of magnesium in 150 ml of THF. This is added dropwise at room temperature to a solution of 10 g of 2-bromothiophene, 3 g of palladium acetate and 1.27 g of triphenylphosphine in 150 ml of THF. The mixture is boiled at reflux under argon for 3.5 hrs., then poured on to ice-water and extracted with ethyl acetate. Chromatography on silica gel (toluene) gives 9.06 g of 2-p-tolyl-thiophene.

Workup

  1. temperatureat reflux under argon for 3.5 hrs
  2. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-62bd2a0202454a9889417e4c682ea257
Source dataset
uspto-grants-2002_08
Patent number
US06441177B1

Reaction notes

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