Styrene → 2-Hydroxy-5-phenylethenyl-N-[3,5-bis(trifluoromethyl)phenyl]benzamide

HRID 2384356Notes

Reaction equation

HRID 2384356 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([NH:13][C:14](=[O:23])[C:15]2[CH:20]=[C:19](I)[CH:18]=[CH:17][C:16]=2[OH:22])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH2:26]=[CH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(NC(C)C)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.CN(C)C=O>[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([NH:13][C:14](=[O:23])[C:15]2[CH:20]=[C:19]([CH:26]=[CH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:18]=[CH:17][C:16]=2[OH:22])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

8

Reactant 4

HCID 7501StyreneHCID 7912DiisopropylamineHCID 80271Tri-o-tolylphosphineHCID 11190699N-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxy-5-iodo-benzamide

Product 1

HCID 728218852-Hydroxy-5-phenylethenyl-N-[3,5-bis(trifluoromethyl)phenyl]benzamideYield 38.3%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of N-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxy-5-iodo-benzamide (475 mg, 1 mmol), styrene (130 mg, 1.25 mmol), palladium acetate (4.5 mg, 0.02 mmol), tris(ortho-tolyl)phosphine (12.2 mg, 0.04 mmol), diisopropylamine (388 mg, 3 mmol) and N,N-dimethylformamide (2 mL) was refluxed for 8 hours. After cooling, water was added to the reaction mixture, and it was extracted with ethyl acetate. After the ethyl acetate layer was washed with water and brine, dried over anhydrous magnesium sulfate and concentrated, the residue was purified by column chromatography on silica gel (hexane-isopropyl ether:2/1→1/1) to give the title compound (173 mg, 38.3%) as a pale yellow solid.

Workup

  1. temperaturewas refluxed for 8 hours
  2. temperatureAfter cooling
  3. extractionwas extracted with ethyl acetate
  4. washAfter the ethyl acetate layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customthe residue was purified by column chromatography on silica gel (hexane-isopropyl ether:2/1→1/1)

Sources & evidence

ORD record
ord-e2b23fa634894b648e1dc0987c452757
Source dataset
uspto-grants-2012_09
Patent number
US08263657B2

Reaction notes

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