1,2-Dimethoxyethane → 1,2-Bis[2-methyl-5-(4-methyl-2-thienyl)-3-thienyl]hexafluorocyclopentene

HRID 3689Notes

Reaction equation

HRID 3689 reaction equation
Br[C:2]1[S:6][C:5]([CH3:7])=[C:4]([C:8]2[C:12]([F:14])([F:13])[C:11]([F:16])([F:15])[C:10]([F:18])([F:17])[C:9]=2[C:19]2[CH:23]=[C:22](Br)[S:21][C:20]=2[CH3:25])[CH:3]=1.[CH3:26][C:27]1[CH:28]=[C:29](OB(O)O)[S:30][CH:31]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:42]([CH2:45]OC)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]>[CH3:25][C:20]1[S:21][C:22]([C:5]2[S:6][CH:2]=[C:42]([CH3:45])[CH:4]=2)=[CH:23][C:19]=1[C:9]1[C:10]([F:17])([F:18])[C:11]([F:15])([F:16])[C:12]([F:13])([F:14])[C:8]=1[C:4]1[CH:3]=[C:2]([C:29]2[S:30][CH:31]=[C:27]([CH3:26])[CH:28]=2)[S:6][C:5]=1[CH3:7]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 149388943,3'-(Perfluorocyclopent-1-ene-1,2-diyl)bis(5-bromo-2-methylthiophene)HCID 544513244-Methyl-2-thienyl boric acid

Product 1

HCID 189352461,2-Bis[2-methyl-5-(4-methyl-2-thienyl)-3-thienyl]hexafluorocyclopentene

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

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 4-methyl-2-thienyl boric acid (852 mg, 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-(4-methyl-2-thienyl)-3-thienyl]hexafluorocyclopentene (447 mg, 0.0008 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-a4ed8d077a2e4b55a7f88a3b17be86f8
Source dataset
uspto-grants-1998_03
Patent number
US05734065

Reaction notes

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