Triisopropylsilyl chloride → (5-Bromo-2-chlorobenzyloxy)triisopropylsilane

HRID 46185Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 46185
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:10])=[C:6]([CH:9]=1)[CH2:7][OH:8].[CH:11]([Si:14](Cl)([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16])([CH3:13])[CH3:12]>CN(C)C=O.CN(C)C1C=CN=CC=1.[Cl-].[NH4+]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:10])=[C:6]([CH:9]=1)[CH2:7][O:8][Si:14]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:11]([CH3:13])[CH3:12]

Komponenten

6

Edukt 2

HCID 139400Triisopropylsilyl chlorideHCID 5074766(5-Bromo-2-chlorophenyl)methanol

Produkt 1

HCID 67153939(5-Bromo-2-chlorobenzyloxy)triisopropylsilaneAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

To a solution of 5-bromo-2-chlorobenzyl alcohol (425 mmol) from Step 2 in N,N-dimethylformamide (400 mL) was added imidazle (58 g, 850 mmol), 4-(dimethylamino)pyridine (2.6 g, 21 mmol), and triisopropylsilyl chloride (136 mL, 638 mmol). The resulting solution was stirred at ambient temperature for 15 h, diluted with a saturated ammonium chloride and extracted with ethyl acetate. The organic layer was washed with water then brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude residue was purified on Biotage® purification apparatus (silica gel, 3 to 10% ethyl acetate in hexanes) to yield the title compound (152 g, 403 mmol, 95%) as a colorless oil.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialbrine, dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified on Biotage® purification apparatus (silica gel, 3 to 10% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-1e71d9299e764e8398e76300701388e8
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541380B2

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