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

HRID 56285

Reaction equation

HRID 56285 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+]>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

5

Reactant 3

HCID 97433-FluorophenolHCID 11430Potassium CarbonateHCID 696322-Bromoacetamide

Product 1

HCID 189381052-(3-Fluorophenoxy)acetamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-fluorophenol (5.61 g, 50.0 mmol), 2-bromoacetamide (7.59 g, 55.0 mmol) and K2CO3 (13.82 g, 100 mmol) in acetone (80 mL) was stirred at 70° C. 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. (7.89 g, 93%)

Workup

  1. temperatureThe mixture was cooled to rt
  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-d042b1f6f2d84485ba161d8dcf4563bd
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Linked notes

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