Ammonium Chloride → tert-Butyldimethylphenoxysilane

HRID 1080568

Reaktionsgleichung

Reaktionsgleichung von HRID 1080568
[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](Br)=[CH:11][C:10]=1F)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Mg].C([Si]1(C2C=CC=CC=2)CCC(=O)CC1)CCCC.[Cl-].[NH4+]>O1CCCC1>[Si:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 110762054-Pentyl-4-phenyl-4-silacyclohexanoneHCID 19593792(4-Bromo-2-fluorophenoxy)(tert-butyl)dimethylsilane

Produkt 1

HCID 529235tert-Butyldimethylphenoxysilane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A Grignard reagent was prepared from 30.5 g of 4-bromo-2-fluorophenol t-butyldimethylsilyl ether and 2.43 g of magnesium in 100 ml of tetrahydrofuran. 20.0 g of 4-n-pentyl-4-phenyl-4-silacyclohexanone was dropped in the resultant solution at 25° C. The reaction mixture was agitated at 25° C. for 5 hours and poured into an ammonium chloride aqueous solution, followed by extraction with ethyl acetate. The ethyl acetate solution was washed with brine, dried and concentrated. 400 ml of benzene and 800 mg of p-toluenesulfonic acid monohydrate were added to the resultant residue, followed by removal of generated water under reflux. When distilling of water was stopped, the benzene solution was concentrated, followed by purification of the resultant residue to obtain 31.6 g (yield: 88%) of 2-fluoro-4-(4-n-pentyl-4-phenyl)-4-sila-1-cyclohexnyl)phenol t-butyldimethylsilyl ether.

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe ethyl acetate solution was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. addition400 ml of benzene and 800 mg of p-toluenesulfonic acid monohydrate were added to the resultant residue
  6. customfollowed by removal of generated water
  7. temperatureunder reflux
  8. distillationWhen distilling of water
  9. concentrationthe benzene solution was concentrated
  10. customfollowed by purification of the resultant residue

Quellen und Nachweise

ORD-Eintrag
ord-384584a357ce4195953cb4e8a7a50a77
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05582765

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