Chloro(chloromethyl)[bis(4-fluorophenyl)]silane → [bis(4-Fluorophenyl)](1H-imidazol-1-ylmethyl)silane

HRID 371314Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 371314
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Si:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)(Cl)[CH2:9]Cl)=[CH:4][CH:3]=1.[NH:19]1[CH:23]=[CH:22][N:21]=[CH:20]1.[K].[H-].C([Al+]CC(C)C)C(C)C>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([SiH:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:9][N:19]2[CH:23]=[CH:22][N:21]=[CH:20]2)=[CH:4][CH:3]=1

Komponenten

7

Edukt 3

HCID 13392398Chloro(chloromethyl)[bis(4-fluorophenyl)]silaneHCID 21225700DiisobutylaluminumhydrideHCID 67086713Potassium imidazole

Produkt 1

HCID 123558487[bis(4-Fluorophenyl)](1H-imidazol-1-ylmethyl)silane

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

To a solution of 3.0 g (9.9 mmol) of bis(4-fluorophenyl)chlorochloromethylsilane and 50 mg of tetrabutylammonium hydrogen sulfate in 10 ml of toluene is added 2.2 g (20.5 mmol) of potassium imidazole. The resulting exotherm is controlled by cooling with ice-water. Th solution is heated at reflux for 5 hours and then was cooled to -70° C. A solution of 10.5 ml (10.5 mmol) of diisobutylaluminum hydride (1.0 molar) in tetrahydrofuran is then added dropwise, and the reaction is warmed to room temperature and quenched by dropwise addition of saturated aqueous ammonium chloride. The solution is diluted with methylene chloride and washed three times with water and once with brine. Drying over magnesium sulfate and removal of solvent gives a viscous oil which is triturated with ether to give the title compound.

Aufarbeitung

  1. temperatureTh solution is heated
  2. temperatureat reflux for 5 hours
  3. temperaturethe reaction is warmed to room temperature
  4. customquenched by dropwise addition of saturated aqueous ammonium chloride
  5. additionThe solution is diluted with methylene chloride
  6. washwashed three times with water
  7. dry with materialDrying over magnesium sulfate and removal of solvent
  8. customgives a viscous oil which
  9. customis triturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-d0061b22668941c1829a4bfb896d9772
Quelldatensatz
uspto-grants-1985_07
Patentnummer
US04530922

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