Water → 4'-Trifluoromethoxy-biphenyl-4-carbaldehyde

HRID 856041Notes

Reaction equation

HRID 856041 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.[CH:13]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)=[O:14].P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>CN(C=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:10][C:9]([F:12])([F:11])[O:8][C:5]1[CH:6]=[CH:7][C:2]([C:18]2[CH:19]=[CH:20][C:15]([CH:13]=[O:14])=[CH:16][CH:17]=2)=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 5210081-Bromo-4-(trifluoromethoxy)benzeneHCID 5910734-Formylphenylboronic Acid

Product 1

HCID 27607204'-Trifluoromethoxy-biphenyl-4-carbaldehydeYield 92.3%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-bromo-4-(trifluoromethoxy)-benzene (1.53 g, 6.35 mmol), 4-formylbenzeneboronic acid (1 g, 6.67 mmol), tetrakis(triphenylphosphine)-palladium (147 mg, 0.13 mmol), and potassium phosphate (2.02 g, 9.53 mmol) in DMF (10 ml) was stirred at 100° C. for 5 hours. The reaction mixture was poured into water, and extracted with ethyl acetate, and the extract was washed with water three times and brine, and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/methylene chloride=3/1) to afford 4′-trifluoromethoxybiphenyl-4-carbaldehyde (1.56 g, yield 92%) as a white powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe extract was washed with water three times and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (n-hexane/methylene chloride=3/1)

Sources & evidence

ORD record
ord-fb57b4f907d141dfadd9d1269d98c181
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

Loading…