Carbon Tetrachloride → 3,3-Dichloro-2-(4-trifluoromethyl-phenyl)-acrylic acid ethyl ester

HRID 1869137Notes

Reaction equation

HRID 1869137 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5](=O)[C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(#N)C.[C:40](Cl)(Cl)([Cl:42])[Cl:41]>>[CH2:1]([O:3][C:4](=[O:17])[C:5]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1)=[C:40]([Cl:42])[Cl:41])[CH3:2]

Participants

5

Reactant 4

HCID 5943Carbon TetrachlorideHCID 6342AcetonitrileHCID 11776TriphenylphosphineHCID 2774410Ethyl alpha-oxo-4-(trifluoromethyl)benzeneacetate

Product 1

HCID 866130793,3-Dichloro-2-(4-trifluoromethyl-phenyl)-acrylic acid ethyl ester

Procedure

680 mg of oxo-(4-trifluoromethyl-phenyl)-acetic acid ethyl ester and 2.2 g of triphenylphosphine are introduced into 8 ml of acetonitrile. 0.8 ml of carbon tetrachloride is then added and the mixture is heated at reflux for 4 hours. The reaction mixture is concentrated completely and the crude product is purified over silica gel. 3,3-Dichloro-2-(4-trifluoromethyl-phenyl)-acrylic acid ethyl ester is obtained. 1H-NMR (CDCl3) 300 MHz: 1.30 (t, 3H), 4.30 (q, 2H), 7.52 (d, 2H), 7.68 (d, 2H).

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 4 hours
  3. concentrationThe reaction mixture is concentrated completely
  4. customthe crude product is purified over silica gel

Sources & evidence

ORD record
ord-8263931664254078ad6833dab9c6b26b
Source dataset
uspto-grants-2009_12
Patent number
US07638514B2

Reaction notes

Loading…