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

HRID 3689
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HRID 3689 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 11979704
Tetrakis(triphenylphosphine)palladium
촉매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a4ed8d077a2e4b55a7f88a3b17be86f8
출처 데이터셋
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05734065

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