Triethylamine → 1-(p-Ethoxyphenyl)-2-(3,4,5-trifluorophenyl)ethene

HRID 375784Notes

Reaction equation

HRID 375784 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[C:4]([F:10])[CH:3]=1.[CH2:11]([O:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[CH2:19])=[CH:16][CH:15]=1)[CH3:12].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>[Pd].C([O-])(=O)C.C(#N)C>[CH2:11]([O:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[CH:19][C:2]2[CH:7]=[C:6]([F:8])[C:5]([F:9])=[C:4]([F:10])[CH:3]=2)=[CH:16][CH:15]=1)[CH3:12]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 795704-EthoxystyreneHCID 80271Tri-o-tolylphosphineHCID 6114091-Bromo-3,4,5-trifluorobenzene

Product 1

HCID 543153741-(p-Ethoxyphenyl)-2-(3,4,5-trifluorophenyl)ethene

Reagents, catalysts & solvents 2

HCID 9793925palladium(I)acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 10.5 g of 1-bromo-3,4,5-trifluorobenzene, 7.4 g of p-ethoxystyrene, 0.25 g of Pd acetate, 0.6 g of tri-o-tolylphosphine, 7 g of triethylamine and 125 ml of acetonitrile is heated at reflux until completion of the reaction. Customary working-up gives 1-(p-ethoxyphenyl)-2-(3,4,5-trifluorophenyl)ethene (C 76 I), which is hydrogenated on PD-C (5%) in THF to give 1-(p-ethoxyphenyl)-2-(3,4,5-trifluorophenyl)ethane, C 45 I.

Workup

  1. temperatureis heated
  2. temperatureat reflux until completion of the reaction

Sources & evidence

ORD record
ord-da8a464857a941818691b76683c84de1
Source dataset
uspto-grants-1996_01
Patent number
US05487845

Reaction notes

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