1,2-Dimethoxyethane → 4'-(Trifluoromethyl)-4-biphenylcarbaldehyde

HRID 505611Notes

Reaction equation

HRID 505611 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[CH:12]([C:14]1[CH:22]=[CH:21][C:17](C(O)=O)=[CH:16][CH:15]=1)=[O:13].C(COC)OC.C(=O)([O-])[O-].[Na+].[Na+]>O.ClCCl>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([C:17]2[CH:21]=[CH:22][C:14]([CH:12]=[O:13])=[CH:15][CH:16]=2)=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 120884-Formylbenzoic acidHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-

Product 1

HCID 27827124'-(Trifluoromethyl)-4-biphenylcarbaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1 g (4.45 mmol) of 1-bromo-4-(trifluoromethyl)benzene and 0.73 g (4.9 mmol) of 4-formylbenzoic acid are added to 30 ml of dimethoxyethane and mixed with 15 ml of 1M sodium carbonate solution. 110 mg of tetrakis (triphenylphosphine)palladium(II) are added, and the mixture is then heated at reflux temperature for 18 hours. The reaction solution is cooled, dichloromethane and water are added, the mixture is filtered through Extrelut and the solvent is distilled off under reduced pressure.

Workup

  1. temperaturethe mixture is then heated
  2. temperatureat reflux temperature for 18 hours
  3. temperatureThe reaction solution is cooled
  4. filtrationthe mixture is filtered through Extrelut
  5. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-22f73463412646c7bc33093989904ab2
Source dataset
uspto-grants-2010_08
Patent number
US07781470B2

Reaction notes

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