Triphenylphosphine → 4-[2-Allyl-2-(4-bromo-phenyl)-pent-4-enyloxy]-4'-trifluoromethyl-biphenyl

HRID 658294Notes

Reaction equation

HRID 658294 reaction equation
[CH2:1]([C:4]([C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=1)([CH2:7][CH:8]=[CH2:9])[CH2:5][OH:6])[CH:2]=[CH2:3].[F:17][C:18]([F:33])([F:32])[C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28](O)=[CH:27][CH:26]=2)=[CH:21][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1.CO>[CH2:1]([C:4]([C:10]1[CH:11]=[CH:12][C:13]([Br:16])=[CH:14][CH:15]=1)([CH2:7][CH:8]=[CH2:9])[CH2:5][O:6][C:28]1[CH:27]=[CH:26][C:25]([C:22]2[CH:23]=[CH:24][C:19]([C:18]([F:17])([F:32])[F:33])=[CH:20][CH:21]=2)=[CH:30][CH:29]=1)[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 155411804-(4-Trifluoromethylphenyl)phenolHCID 674858602-Allyl-2-(4-bromo-phenyl)-pent-4-en-1-ol

Product 1

HCID 674857154-[2-Allyl-2-(4-bromo-phenyl)-pent-4-enyloxy]-4'-trifluoromethyl-biphenylYield 61%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

A solution of 2-allyl-2-(4-bromo-phenyl)-pent-4-en-1-ol (from Preparation 3, Step B)(0.206 g, 0.734 mmol), 4′-trifluoromethyl-biphenyl-4-ol (0.184 g, 0.772 mmol), and triphenylphosphine (0.286 g, 1.09 mmol) in toluene (7.0 mL) is treated with 1,1′-(azodicarbonyl)-dipiperidine (0.272 g, 1.08 mmol) and stirred overnight at room temperature. The reaction is then warmed to 80° C. for 6 h, cooled to room temperature, diluted with MeOH, and concentrated. The residue is loaded onto silica gel and eluted with hexanes using a gradient of 0% EtOAc to 50% EtOAc to provide 0.226 g, (61%) of the title compound as a yellow syrup. 1H NMR (CDCl3): δ 7.66-7.61 (m, 4H), 7.52-7.50 (m, 2H), 7.46-7.44 (m, 2H), 7.24-7.22 (m, 2H), 7.00-6.98 (m, 2H), 5.56 (ddt, J=17.1, 10.3, 7.2 Hz, 2H), 5.05-4.99 (m, 4H), 4.12 (s, 2H), 2.61 (d, J=7.4 Hz, 4H).

Workup

  1. temperatureThe reaction is then warmed to 80° C. for 6 h
  2. temperaturecooled to room temperature
  3. concentrationconcentrated
  4. washeluted with hexanes using a gradient of 0% EtOAc to 50% EtOAc

Sources & evidence

ORD record
ord-7b0afeacbff14e54b4369b716307c83e
Source dataset
uspto-grants-2011_12
Patent number
US08076374B2

Reaction notes

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