3-Fluorophenol → 2-(3-Fluorophenoxy)acetamide

HRID 56278

Reaction equation

HRID 56278 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Br[CH2:10][C:11]([NH2:13])=[O:12].C([O-])([O-])=O.[K+].[K+].C([O-])([O-])=O.[Cs+].[Cs+]>CC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:10][C:11]([NH2:13])=[O:12]

Participants

6

Reactant 4

HCID 97433-FluorophenolHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 696322-Bromoacetamide

Product 1

HCID 189381052-(3-Fluorophenoxy)acetamideYield 30%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-fluorophenol (11.2 g, 100 mmol), 2-bromoacetamide (13.8 g, 100 mmol), K2CO3 (13.82 g, 100 mmol) and Cs2CO3 (32.58 g, 100 mmol) in acetone (150 mL) was refluxed overnight. The mixture was cooled to rt and filtered and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a white solid (5.06 g, 30%).

Workup

  1. temperaturewas refluxed overnight
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1)

Sources & evidence

ORD record
ord-7eb07fbcc8ef449b86ac184e3c4a8ea6
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Linked notes

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