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Triethylamine → (4-Bromo-thiophen-2-ylethynyl)-trimethyl-silane

HRID 1916729
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HRID 1916729 반응식
C(N(CC)CC)C.Br[C:9]1[S:10][CH:11]=[C:12]([Br:14])[CH:13]=1.[C:15]([Si:17]([CH3:20])([CH3:19])[CH3:18])#[CH:16]>C1COCC1.[Cu]I>[Br:14][C:12]1[CH:13]=[C:9]([C:16]#[C:15][Si:17]([CH3:20])([CH3:19])[CH3:18])[S:10][CH:11]=1
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참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 2724560Thiophene, 2,4-dibromo-

생성물 1

HCID 67364285(4-Bromo-thiophen-2-ylethynyl)-trimethyl-silane

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8028
Tetrahydrofuran
용매
2회

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온도
-78 °C

실험 절차

Under an argon atmosphere 0.37 g (1.94 mmol) CuI, 2.24 g (1.94 mmol) tetrakis-triphenylphosphane-palladium and 16.2 mL triethylamine are added to a solution of 10.0 g (38.85 mmol) 2,4-dibromothiophene in 300 mL THF, the reaction mixture is cooled to −78° C. and then at this temperature a solution of 5.6 mL (38.85 mmol)) ethynyl-trimethyl-silane in 250 mL THF is slowly added dropwise. After the addition has ended the mixture is allowed to heat up slowly to RT and stirred overnight. The mixture is evaporated down i. vac., the residue is combined with water, extracted exhaustively with DCM and the combined organic phases are dried over MgSO4. After the desiccant and solvent have been eliminated the residue is triturated with PE, filtered to remove insoluble ingredients and the solvent is evaporated down. The residue is purified by chromatography (silica gel, PE).

후처리

  1. additionAfter the addition
  2. temperatureto heat up slowly to RT
  3. customThe mixture is evaporated down i
  4. extractionextracted exhaustively with DCM
  5. dry with materialthe combined organic phases are dried over MgSO4
  6. customis triturated with PE
  7. filtrationfiltered
  8. customto remove insoluble ingredients
  9. customthe solvent is evaporated down
  10. customThe residue is purified by chromatography (silica gel, PE)

출처 및 근거

ORD 기록
ord-82ac90d412004c0bada85eec69d02634
출처 데이터셋
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08618132B2

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