N-Butylchlorodimethylsilane → (4-Bromophenylethynyl)-n-butyldimethylsilane

HRID 1692159

Reaktionsgleichung

Reaktionsgleichung von HRID 1692159
C([Mg]Br)(C)C.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[CH:14])=[CH:9][CH:8]=1.[CH2:15]([Si:19](Cl)([CH3:21])[CH3:20])[CH2:16][CH2:17][CH3:18]>C1COCC1>[Br:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][Si:19]([CH2:15][CH2:16][CH2:17][CH3:18])([CH3:21])[CH3:20])=[CH:9][CH:8]=1

Komponenten

5

Edukt 3

HCID 66079N-ButylchlorodimethylsilaneHCID 136603Benzene, 1-bromo-4-ethynyl-HCID 178418365HCID 178418365, Verbindung

Produkt 1

HCID 66905447(4-Bromophenylethynyl)-n-butyldimethylsilaneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

i-propylmagnesiumbromide (0.67 M/THF solution, 3.10 mL, 2.1 mmol) was added dropwise to THF solution (15 mL) of 1-bromo-4-ethynylbenzene (382 mg, 2.0 mmol) at 0° C. After the mixture was stirred for 20 minutes, an ice water bath was removed. After stirring at room temperature for 10 minutes, n-butyldimethylsilyl chloride (0.69 mL, 4.0 mmol) was added to the mixture. After stirring for 2 hours, the reaction was terminated by the addition of saturated ammonium chloride solution (5 mL). The reaction mixture was extracted with ethyl acetate, and it was concentrated and thereafter purified by means of flash column chromatography to obtain (4-bromophenylethynyl)-n-butyldimethylsilane (530 mg, isolated yield: 90%).

Aufarbeitung

  1. customan ice water bath was removed
  2. stirringAfter stirring at room temperature for 10 minutes
  3. stirringAfter stirring for 2 hours
  4. customthe reaction was terminated by the addition of saturated ammonium chloride solution (5 mL)
  5. extractionThe reaction mixture was extracted with ethyl acetate, and it
  6. concentrationwas concentrated
  7. custompurified by means of flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1873323f6ad14c0abe110cf23c88ae64
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153835B2

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