Potassium Carbonate → 2,6-Dimethyl-4'-trifluoromethyl-biphenyl-4-carbaldehyde

HRID 251307Notes

Reaction equation

HRID 251307 reaction equation
[CH:1]([C:3]1[CH:8]=[C:7]([CH3:9])[C:6](OS(C(F)(F)F)(=O)=O)=[C:5]([CH3:18])[CH:4]=1)=[O:2].[F:19][C:20]([F:31])([F:30])[C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.[Li+].[Cl-].C([O-])([O-])=O.[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:18][C:5]1[CH:4]=[C:3]([CH:1]=[O:2])[CH:8]=[C:7]([CH3:9])[C:6]=1[C:24]1[CH:25]=[CH:26][C:21]([C:20]([F:31])([F:30])[F:19])=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 544771104-Formyl-2,6-dimethylphenyl trifluoromethanesulfonate

Product 1

HCID 860853062,6-Dimethyl-4'-trifluoromethyl-biphenyl-4-carbaldehydeYield 96.2%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Trifluoro-methanesulfonic acid 4-formyl-2,6-dimethyl-phenyl ester (4 g, 14.2 mmol), 4-trifluoromethyl-phenylboronic acid (5.4 g, 28.4 mmol), tetrakis(triphenylphosphine)palladium (1.64 g, 1.42 mmol), LiCl (1.8 g, 42.6 mmol), and K2CO3 (5.9 g, 42.6 mmol) are placed in a flask. The system is purged with nitrogen, followed by the addition of toluene (20 ml) and water (5 ml). The resulting mixture is refluxed overnight, loaded on silica gel directly, and purified by silica gel column chromatography, eluting with EtOAc/hexanes to afford 3.8 g (96%) of the titled compound as a white solid. 1H-NMR.

Workup

  1. customThe system is purged with nitrogen
  2. additionfollowed by the addition of toluene (20 ml) and water (5 ml)
  3. temperatureThe resulting mixture is refluxed overnight
  4. custompurified by silica gel column chromatography
  5. washeluting with EtOAc/hexanes

Sources & evidence

ORD record
ord-3b46b7aad42a419ab7bb1e1121eb0808
Source dataset
uspto-grants-2011_01
Patent number
US07863329B2

Reaction notes

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