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3,4-Dibromothiophene → 3,4-Bis(trimethylsilylethynyl)thiophene

HRID 493445
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HRID 493445 반응식
Br[C:2]1[C:6](Br)=[CH:5][S:4][CH:3]=1.[CH3:8][Si:9]([C:12]#[CH:13])([CH3:11])[CH3:10].O1[CH2:18][CH2:17]CC1.C(NC(C)C)(C)C>[Cu](I)I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:8][Si:9]([C:12]#[C:13][C:2]1[C:6]([C:17]#[C:18][Si:9]([CH3:11])([CH3:10])[CH3:8])=[CH:5][S:4][CH:3]=1)([CH3:11])[CH3:10]
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참가 물질

6

반응물 3

HCID 184523,4-DibromothiopheneHCID 66111TrimethylsilylacetyleneHCID 18968793THF diisopropylamine

생성물 1

HCID 576816483,4-Bis(trimethylsilylethynyl)thiophene

시약·촉매·용매 2

HCID 11776Triphenylphosphine촉매HCID 83717Copper iodide촉매

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온도
70 °C

실험 절차

2.5 ml (22.6 mmol) of 3,4-dibromothiophene, commercially available from Aldrich under the Product No. 24, 715-4, and 8 ml (56.5 mmol) of trimethylsilylacetylene were mixed with a solvent of tetrahydrofuran/diisopropylamine (1:1), and 0.15 g (0.23 mmol) of palladium dichlorodiphosphine, 21 mg (0.11 mmol) of copper iodide and 0.1 g (0.36 mmol) of triphenylphosphine were then sequentially added thereto. The reaction solution was heated at 70° C. for 8 hours, and washed with an aqueous solution of ammonium chloride. The resulting organic layer was dried over magnesium sulfate, dried under reduced pressure, and purified using silica gel column chromatography, thus obtaining 1.5 g of 3,4-bis(trimethylsilylethynyl)thiophene (IIa).

후처리

  1. additionwere then sequentially added
  2. washwashed with an aqueous solution of ammonium chloride
  3. dry with materialThe resulting organic layer was dried over magnesium sulfate
  4. customdried under reduced pressure
  5. custompurified

출처 및 근거

ORD 기록
ord-92ab3581d50b4be2b032232b2d2cd629
출처 데이터셋
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07534899B2

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