Ethanol → Ethyl 3-(2-fluorophenyl)prop-2-enoate

HRID 1954872

Reaction equation

HRID 1954872 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([OH:8])=[O:7].S(Cl)(Cl)=O.[CH2:17](O)[CH3:18]>>[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([O:8][CH2:17][CH3:18])=[O:7]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 679773-(2-Fluorophenyl)prop-2-enoic acid

Product 1

HCID 590919Ethyl 3-(2-fluorophenyl)prop-2-enoateYield 96%

Procedure

A solution of 2-fluorocinnamic acid (48.4 g, 0.29 mol, Aldrich) and thionyl chloride (5 mL) in ethanol (650 mL) was heated to reflux for 48 h. The mixture was concentrated in vacuo. The residue was taken up in ethyl acetate, washed successively with a 5% aqueous sodium bicarbonate solution, water and brine, and dried (Na2SO4). Filtration and concentration gave 54.25 g (96%) of crude ethyl 2-fluorocinnamate. This material was used without further purification.

Workup

  1. temperatureto reflux for 48 h
  2. concentrationThe mixture was concentrated in vacuo
  3. washwashed successively with a 5% aqueous sodium bicarbonate solution, water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-8bfdc6d8a8e54db8afd05c5974aad121
Source dataset
uspto-grants-2000_09
Patent number
US06124284

Linked notes

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