Reaktion #84552

ord-aa565b51f54e4f788b914aab720434e4

Reaktionsgleichung

O
water
Oc1cccc(F)c1
3-fluorophenol
CCOC(=O)C(C)(C)Br
ethyl 2-bromo-2-methylpropanoate
O=C([O-])[O-].[K+].[K+]
K2CO3
CCOC(=O)C(C)(C)Oc1cccc(F)c1
title compound
Ausbeute 47.1%
CCOC(=O)C(C)(C)Oc1cccc(F)c1
ethyl 2-(3-fluorophenoxy)-2-methylpropanoate
Ausbeute 47.1%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturwas refluxed overnight
  2. 2
    ExtraktionThe resulting mixture was extracted with DCM (40 mL×2)
  3. 3
    WaschenThe combined organic phases were washed with brine (40 mL×2)
  4. 4
    Trocknendried over anhydrous Na2SO4
  5. 5
    Einengenconcentrated in vacuo
  6. 6
    SonstigeThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1)

Vorschrift

A mixture of 3-fluorophenol (3.36 g, 30.0 mmol), ethyl 2-bromo-2-methylpropanoate (8.78 g, 45.0 mmol) and K2CO3 (6.22 g, 45.0 mmol) in acetone (50 mL) was refluxed overnight. The mixture was cooled to rt and 60 mL of water was added. The resulting mixture was extracted with DCM (40 mL×2). The combined organic phases were washed with brine (40 mL×2), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1) to give the title compound as colorless liquid (3.20 g, 47%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09434695B2uspto-grants-2016_09