4-Bromophenol → 1-(4-Ethoxyphenyl)-2-(4'-difluoromethoxyphenyl)-ethene

HRID 274166Notes

Reaction equation

HRID 274166 reaction equation
[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[CH2:9])=[CH:6][CH:5]=1)[CH3:2].[F:12][CH:13]([F:22])[O:14][C:15]1[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=1.BrC1C=CC(O)=CC=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[CH:9][C:18]2[CH:19]=[CH:20][C:15]([O:14][CH:13]([F:22])[F:12])=[CH:16][CH:17]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

8

Reactant 4

HCID 78084-BromophenolHCID 795704-EthoxystyreneHCID 80271Tri-o-tolylphosphineHCID 27370071-Bromo-4-(difluoromethoxy)benzene

Product 1

HCID 540575161-(4-Ethoxyphenyl)-2-(4'-difluoromethoxyphenyl)-ethene

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

22.2 g of 4-ethoxystyrene, 33.5 g of 4-(difluoromethoxy)bromobenzene (available from 4-bromophenol analogously to Example 1)), 0.67 g of palladium(II) acetate, 20.8 ml of triethylamine and 1.83 g of tri-o-tolylphosphine are heated to boiling in 225 ml of acetonitrile for 24 hours. After cooling to 0° C., the crystals are filtered off with suction and washed with acetonitrile and water. m.p.: 177° C.

Workup

  1. filtrationthe crystals are filtered off with suction
  2. washwashed with acetonitrile and water

Sources & evidence

ORD record
ord-5b93b3548ec64261a190c59d881a3eaa
Source dataset
uspto-grants-1995_02
Patent number
US05389292

Reaction notes

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