3-Bromophenol → tert-Butyl 2-(3-bromophenoxy)acetate

HRID 2373178Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2373178
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[C:11]([O:15][C:16](=[O:19])[CH2:17]Br)([CH3:14])([CH3:13])[CH3:12]>CN(C)C=O>[C:11]([O:15][C:16](=[O:19])[CH2:17][O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)([CH3:14])([CH3:13])[CH3:12]

Komponenten

5

Edukt 3

HCID 115633-BromophenolHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetate

Produkt 1

HCID 20577391tert-Butyl 2-(3-bromophenoxy)acetateAusbeute 85,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

3-Bromophenol (20.4 g, 118 mmol) dissolved in dry N,N-dimethylformamide was carefully treated with sodium hydride (4 g, 167 mmol). t-Butylbromoacetate (23 g, 118 mmol) was added and the mixture heated to 75° C. for 90 minutes. The reaction was concentrated in vacuo and the residue partitioned between ethyl acetate and water. The organic phase was washed with saturated ammonium acetate and concentrated in vacuo to yield 28.9 g of tert-butyl(3-bromophenoxy)acetate.

Aufarbeitung

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe residue partitioned between ethyl acetate and water
  3. washThe organic phase was washed with saturated ammonium acetate
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e920f48d36b742e68feb51f8600f22cc
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07459454B2

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