Potassium Carbonate → (Z)-methyl 3-(2-(3,4-difluorophenoxy)acetamido)but-2-enoate

HRID 56242

Reaction equation

HRID 56242 reaction equation
C([O-])([O-])=O.[K+].[K+].[F:7][C:8]1[CH:9]=[C:10]([OH:15])[CH:11]=[CH:12][C:13]=1[F:14].[CH3:16][O:17][C:18](=[O:27])/[CH:19]=[C:20](\[NH:22][C:23](=[O:26])[CH2:24]Br)/[CH3:21]>CC(C)=O>[F:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][C:13]=1[F:14])[O:15][CH2:24][C:23]([NH:22]/[C:20](/[CH3:21])=[CH:19]\[C:18]([O:17][CH3:16])=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 759273,4-DifluorophenolHCID 90023822Methyl 3-(2-bromoacetamido)crotonate

Product 1

HCID 90023321(Z)-methyl 3-(2-(3,4-difluorophenoxy)acetamido)but-2-enoateYield 59.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of K2CO3 (1.38 g, 10.0 mmol) in acetone (50 mL) were added 3,4-difluorophenol (0.78 g, 6.00 mmol) and (Z)-methyl-3-(2-bromoacetamido)but-2-enoate (1.18 g, 5.00 mmol) and the mixture was refluxed for 5 h. The mixture was cooled to rt and filtered and the filtrate was concentrated in vacuo. To the residue was added DCM (100 mL) and the mixture was washed with water (100 mL×2) and brine (100 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=5:1) to give the title compound as a white solid (0.85 g, 59%).

Workup

  1. temperaturethe mixture was refluxed for 5 h
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionTo the residue was added DCM (100 mL)
  5. washthe mixture was washed with water (100 mL×2) and brine (100 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=5:1)

Sources & evidence

ORD record
ord-ed3ce17cf6f94013ac2c4e9d743868d2
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Linked notes

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