Triethylamine → 3-[[Dimethyl(1,1,2-trimethylpropyl)silyl]oxy]benzene bromide

HRID 465872

Reaktionsgleichung

Reaktionsgleichung von HRID 465872
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH3:16][Si:17](Cl)([CH3:24])[C:18]([CH:21]([CH3:23])[CH3:22])([CH3:20])[CH3:19]>C(Cl)Cl.CN(C)C1C=CN=CC=1.CCCCCC>[Br-:1].[CH3:16][Si:17]([CH3:24])([C:18]([CH3:20])([CH3:19])[CH:21]([CH3:23])[CH3:22])[O:8][C:4]1[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=1

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 115633-BromophenolHCID 144239Dimethylthexylsilyl chloride

Produkt 1

HCID 198754073-[[Dimethyl(1,1,2-trimethylpropyl)silyl]oxy]benzene bromideAusbeute 94,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-bromophenyl alcohol (5.0 g, 26.7 mmol) and triethylamine (3.25 g, 32.1 mmol) in anhydrous CH2Cl2 (125 mL) at room temperature under argon was added dropwise dimethylthexylsilylchloride (5.26 g, 29.4 mmol). After 1.5 hours, 4-dimethylaminopyridine (0.50 g) was added and the stirring was continued for an additional 3 hours. The reaction mixture was diluted with hexane (200 mL) and the precipitate was filtered off. The filtrate was concentrated, partitioned between hexane (200 mL) and 1N aqueous HCl (3×40 mL), and the organic layer was washed with saturated aqueous NaHCO3 (2×40 mL). The organic layer was dried (MgSO4), filtered and concentrated to yield title bromide (8.01 g, 91%).

Aufarbeitung

  1. waitthe stirring was continued for an additional 3 hours
  2. filtrationthe precipitate was filtered off
  3. concentrationThe filtrate was concentrated
  4. custompartitioned between hexane (200 mL) and 1N aqueous HCl (3×40 mL)
  5. washthe organic layer was washed with saturated aqueous NaHCO3 (2×40 mL)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2120ce38006b45ea849d9d008495a88d
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05153327

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