Triethylamine → Triphenyl-(2,4,6-trichlorophenylethynyl)silane

HRID 735085노트

반응식

HRID 735085 반응식
Br[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[CH:4][C:3]=1[Cl:10].[C:11]1([Si:17]([C:30]#[CH:31])([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>O1CCOCC1.[Cu]I>[C:24]1([Si:17]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:30]#[C:31][C:2]2[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[CH:4][C:3]=2[Cl:10])[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 1405262-Bromo-1,3,5-trichlorobenzeneHCID 642601(Triphenylsilyl)acetylene

생성물 1

HCID 86060684Triphenyl-(2,4,6-trichlorophenylethynyl)silane

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 312751,4-Dioxane용매

실험 절차

In an argon atmosphere, 9 g (34.6 mmol) of 1-bromo-2,4,6-trichlorobenzene, 9.8 g (34.45 mmol) of triphenylsilylacetylene, and 15 mL of triethylamine are dissolved in 100 mL of absolute dioxane and at 90° C. combined with 0.2 g (1.04 mmol) of copper (I) iodide and 1.2 g (1.04 mmol) of tetrakistriphenylphosphine palladium and stirred for 20 hours. The reaction mixture is filtered through CELITE® filter aid and the filtrate is evaporated down. The residue is taken up in ethyl acetate and extracted with water. The organic phase is dried over sodium sulfate. The purification is carried out by column chromatography on silica gel (eluant: petroleum ether/toluene (5:1)). The product is recrystallized from petroleum ether and dried in the vacuum drying chamber at 70° C. Yield: 6.9 g (43% of theory); melting point: 115° C.-120° C.; C26H17Cl3Si (M=463.87); calc.: molecular ion peak (M+H)+: 463/465/467/469; found: molecular ion peak (M+H)+: 463/465/467/469; Rf value: 0.6 (silica gel, petroleum ether/toluene (4:1)).

후처리

  1. filtrationThe reaction mixture is filtered through CELITE®
  2. filtrationfilter aid
  3. customthe filtrate is evaporated down
  4. extractionextracted with water
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. customThe purification
  7. customThe product is recrystallized from petroleum ether
  8. customdried in the vacuum
  9. customdrying chamber at 70° C

출처 및 근거

ORD 기록
ord-32f5de46a19b44a3a11dfaffc5a41dc8
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592373B2

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