3-Fluorophenol → Ethyl 2,2-difluoro-2-(3-fluorophenoxy)acetate

HRID 56294

Reaction equation

HRID 56294 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Br[C:10]([F:17])([F:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12].C([O-])([O-])=O.[K+].[K+]>CO>[F:16][C:10]([F:17])([O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 3

HCID 97433-FluorophenolHCID 11430Potassium CarbonateHCID 69585Ethyl bromodifluoroacetate

Product 1

HCID 66455005Ethyl 2,2-difluoro-2-(3-fluorophenoxy)acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-fluorophenol (2.24 g, 20.0 mmol), ethyl 2-bromo-2,2-difluoroacetate (8.12 g, 40.0 mmol) and K2CO3 (6.91 g, 50.0 mmol) in MeOH (20 mL) was stirred at 70° C. overnight. It was then cooled to rt and filtered and the filtrate was concentrated in vacuo to give the title compound, which was used for next step without further purification.

Workup

  1. temperatureIt was then cooled to rt
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-47bd33ea822e493bb4ab17fa47d0f8ef
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Linked notes

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