Potassium Carbonate → 1H,2H-Hexafluorocyclopentene

HRID 3690Notes

Reaction equation

HRID 3690 reaction equation
BrC1SC(C)=C([C:8]2[C:12]([F:14])([F:13])[C:11]([F:16])([F:15])[C:10]([F:18])([F:17])[C:9]=2C2C=C(Br)SC=2C)C=1.C[Si](C)(C)C1SC(C2SC(OB(O)O)=CC=2)=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.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.[Pd]>[F:13][C:12]1([F:14])[CH:8]=[CH:9][C:10]([F:18])([F:17])[C:11]1([F:15])[F:16]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 149388943,3'-(Perfluorocyclopent-1-ene-1,2-diyl)bis(5-bromo-2-methylthiophene)HCID 540859315-(5-Trimethylsilyl-2-thienyl)-2-thienyl boric acid

Product 1

HCID 113098221H,2H-HexafluorocyclopenteneYield 35%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

1,2-bis(5-bromo-2-methyl-3-thienyl)hexafluorocyclopentene (1.0 g, 0.002 mol) was dissolved in dimethoxyethane (50 ml), and palladium tetra(triphenylphosphine) (120 mg) was added to the mixture which was stirred for 5 minutes under argon atmosphere. With 5-(5-trimethylsilyl-2-thienyl)-2-thienyl boric acid (1.4 g, 0.006 mol) and an aqueous solution of potassium carbonate (0.1 mol dm-3, 10 ml) were added, the reaction mixture was refluxed for two hours. It was then concentrated under reduced pressures, extracted with diethylether and rinsed with water. With the diethylether removed under reduced pressures, the product was purified by alumina column chromatogram to give 1,2-bis[2-methyl-5{5-trimethylsilyl-2-thienyl)-2-thienyl}-3-thienyl]hexafluorocyclopentene (550 mg, 0.0007 mol).

Workup

  1. temperaturethe reaction mixture was refluxed for two hours
  2. concentrationIt was then concentrated under reduced pressures
  3. extractionextracted with diethylether
  4. washrinsed with water
  5. customWith the diethylether removed under reduced pressures
  6. customthe product was purified by alumina column chromatogram

Sources & evidence

ORD record
ord-197bcc85a93f490aae992086e3528101
Source dataset
uspto-grants-1998_03
Patent number
US05734065

Reaction notes

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