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

HRID 362827Notes

Reaction equation

HRID 362827 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-779241cd286b412d9ca627535625ecf0
Source dataset
uspto-grants-1999_02
Patent number
US05872118

Reaction notes

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