Methyl iodide → Methyl (E)-3-fluorocinnamate

HRID 2242561Notes

Reaction equation

HRID 2242561 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)/[CH:5]=[CH:6]/[C:7]([OH:9])=[O:8].IC.[C:15](=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O.C(OCC)(=O)C>[CH3:15][O:8][C:7](=[O:9])/[CH:6]=[CH:5]/[C:4]1[CH:10]=[CH:11][CH:12]=[C:2]([F:1])[CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 1551219(2E)-3-(3-Fluorophenyl)-2-propenoic acid

Product 1

HCID 13415099Methyl (E)-3-fluorocinnamateYield 87.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a mixture of trans-3-fluorocinnamic acid (50 g, 300 mmol) and iodomethane (300 mL) in acetone (1 L) was added portion wise cesium carbonate (147 g, 450 mmol, 1.5 equivalents), and the mixture was heated at 65° C. for 1.5 hours in a sealed reaction vessel. Upon cooling to room temperature, the reaction mixture was diluted with ethyl acetate (1 L), filtered through a pad of silica gel, and concentrated to give 47.33 g (87%) of trans-3-fluorocinnamic acid methyl ester as a colorless oil. MS (ES) m/z 180.0 (M+•).

Workup

  1. temperatureUpon cooling to room temperature
  2. filtrationfiltered through a pad of silica gel
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-fbba6b4c007244a98e2931dc4a5284df
Source dataset
uspto-grants-2010_03
Patent number
US07671238B2

Reaction notes

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