Ethyl Acetate → 3-Fluoromethoxy-2-(o-tolyl)-acrylic acid methyl ester

HRID 726848Notes

Reaction equation

HRID 726848 reaction equation
Br[CH2:2][F:3].[Na].[CH3:5][O:6][C:7](=[O:18])[C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])=[CH:9][OH:10].C(OCC)(=O)C>CN(C)C=O>[CH3:5][O:6][C:7](=[O:18])[C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])=[CH:9][O:10][CH2:2][F:3]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 61108BromofluoromethaneHCID 5360545SodiumHCID 67027340Methyl 2-(2-methyl phenyl)-3-hydroxy-2-propenoate

Product 1

HCID 544607813-Fluoromethoxy-2-(o-tolyl)-acrylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 14.9 g of bromofluoromethane in 20 ml of dimethylformamide is added dropwise at 10° C. to a solution of 20 g of the sodium salt of 3-hydroxy-2-(o-tolyl)-acrylic acid methyl ester in 125 ml of dimethylformamide and the reaction mixture is then stirred at room temperature for 2.5 hours. The reaction mixture is then poured onto 400 ml of ice-water and exhaustive extraction is carried out with ethyl acetate. Washing with saturated sodium chloride solution is followed by drying over sodium sulfate, filtering and concentration by evaporation. Chromatography on silica gel with hexane/ethyl acetate (6:1) yields pure 3-fluoromethoxy-2-(o-tolyl)-acrylic acid methyl ester in the form of a colourless oil.

Workup

  1. washWashing with saturated sodium chloride solution
  2. dry with materialby drying over sodium sulfate
  3. filtrationfiltering
  4. concentrationconcentration
  5. customby evaporation

Sources & evidence

ORD record
ord-32c98a3795e44e20ad625a48b8d80d49
Source dataset
uspto-grants-1998_01
Patent number
US05710314

Reaction notes

Loading…