Chloride → Ethyl 3-chloro-4-trifluoromethylcinnamate
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl-].[I-].[Na+].[C:35]([O:39][CH2:40][CH3:41])(=[O:38])[CH:36]=[CH2:37]>CN(C)C=O.[Ni](Br)Br.C(N(CC)CC)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10])[CH:37]=[CH:36][C:35]([O:39][CH2:40][CH3:41])=[O:38]Participants
9
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 140 °C
Procedure
A suspension of 3.5 g of 2,4-dichlorobenzotrifluoride, 1.28 g of triphenylphosphine, 865 mg of paradium(II) chloride, 2.68 g of sodium iodide, 712 mg of nickel(II) bromide, 4.94 g of triethylamine, and 1.79 g of ethyl acrylate in 16 ml of N,N-dimethylformamide was heated at 140° C. for over night in a sealed tube. The reaction mixture was filtrated off, and the filtrate was concentrated under a reduced pressure. The residue was extracted with ethyl acetate, the extract was washed with water, dried, and evaporated under a reduced pressure. The resulting residue was purified by a silica gel column chromatography to give 1.12 g of ethyl 3-chloro-4-trifluoromethylcinnamate.
Workup
- filtrationThe reaction mixture was filtrated off
- concentrationthe filtrate was concentrated under a reduced pressure
- extractionThe residue was extracted with ethyl acetate
- washthe extract was washed with water
- customdried
- customevaporated under a reduced pressure
- customThe resulting residue was purified by a silica gel column chromatography
Sources & evidence
- ORD record
- ord-6626cf1b872c47869f0e7a6cb26ae6f8
- Source dataset
- uspto-grants-1994_03
- Patent number
- US05294718
Reaction notes
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