3-Fluorophenol → Methyl 3-(2-(3-fluorophenoxy)acetamido)crotonate

HRID 56135Notes

Reaction equation

HRID 56135 reaction equation
C([O-])([O-])=O.[K+].[K+].[F:7][C:8]1[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1.Br[CH2:16][C:17]([NH:19]/[C:20](/[CH3:26])=[CH:21]\[C:22]([O:24][CH3:25])=[O:23])=[O:18]>CC(C)=O>[F:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=1)[O:14][CH2:16][C:17]([NH:19]/[C:20](/[CH3:26])=[CH:21]\[C:22]([O:24][CH3:25])=[O:23])=[O:18]

Participants

5

Reactant 3

HCID 97433-FluorophenolHCID 11430Potassium CarbonateHCID 90023822Methyl 3-(2-bromoacetamido)crotonate

Product 1

HCID 90022556Methyl 3-(2-(3-fluorophenoxy)acetamido)crotonateYield 70%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of K2CO3 (0.37 g, 2.68 mmol) in acetone (10 mL) were added 3-fluorophenol (0.30 g, 2.68 mmol) and methyl 3-(2-bromoacetamido)crotonate (0.76 g, 3.22 mmol), the mixture was refluxed for 5 h and cooled to rt. The mixture was concentrated in vacuo and the residue was dissolved in CH2Cl2 (40 mL), washed with brine (40 mL×3). The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=10:1) to give the title compound as a yellowish solid (0.50 g, 70%).

Workup

  1. temperaturethe mixture was refluxed for 5 h
  2. concentrationThe mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in CH2Cl2 (40 mL)
  4. washwashed with brine (40 mL×3)
  5. dry with materialThe organic phase was dried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=10:1)

Sources & evidence

ORD record
ord-6c3a875562504500adf1829f9f1351b8
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

Loading…