Sodium Carbonate → 2-(2-methylphenyl)thiophene

HRID 1166935Notes

Reaction equation

HRID 1166935 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH3:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1B(O)O.Br[C:18]1[S:19][CH:20]=[CH:21][CH:22]=1>C1(C)C=CC=CC=1.C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:8]1([CH3:7])[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:18]1[S:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 138512-BromothiopheneHCID 27332672-Methylphenyl boronic acid

Product 1

HCID 35641892-(2-methylphenyl)thiopheneYield 344.3%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

Sodium carbonate (5 ml., 2M aqueous solution) followed by 2-methylphenylboronic acid (0.294 g, 2.4 mmol) were added to a solution of 2-bromothiophene (0.542 g, 2 mmol) and tetrakis(triphenylphosphine)-palladium(0) (100 mg) in toluene (5 ml) and ethanol (5 ml) under nitrogen. The mixture was refluxed for 2 hours, cooled to room temperature and extracted with ethyl acetate (2×50 ml). The combined organic layers was dried over MgSO4 and evaporated. The residue was flash chromatographed on silica gel using hexane as eluent to afford 1.2 g of 2-(2-tolyl)thiophene as a colorless gum.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. extractionextracted with ethyl acetate (2×50 ml)
  3. dry with materialThe combined organic layers was dried over MgSO4
  4. customevaporated
  5. customchromatographed on silica gel

Sources & evidence

ORD record
ord-c04e039b09e84294b7787539df3cecb7
Source dataset
uspto-grants-2003_09
Patent number
US06613804B2

Reaction notes

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