Potassium Phosphate, Tribasic → 2'-Fluoro-2-formyl-5'-methoxy-biphenyl-4-carboxylic acid methyl ester

HRID 404364Notes

Reaction equation

HRID 404364 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1OS(C(F)(F)F)(=O)=O)[C:6]([O:8][CH3:9])=[O:7])=[O:2].[F:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:23]=1B(O)O.[O-]P([O-])([O-])=O.[K+].[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>[CH3:9][O:8][C:6]([C:5]1[CH:10]=[CH:11][C:12]([C:23]2[CH:24]=[C:25]([O:28][CH3:29])[CH:26]=[CH:27][C:22]=2[F:21])=[C:3]([CH:1]=[O:2])[CH:4]=1)=[O:7]

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 41572112-Fluoro-5-methoxyphenylboronic acidHCID 57467631Methyl 3-formyl-4-(trifluoromethylsulfonyloxy)benzoate

Product 1

HCID 574676302'-Fluoro-2-formyl-5'-methoxy-biphenyl-4-carboxylic acid methyl esterYield 100.6%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
90 °C

Procedure

To a round bottle flask, was added methyl 3-formyl-4-(trifluoromethylsulfonyloxy)benzoate (6300 mg, 20 mmol), 2-fluoro-5-methoxyphenylboronic acid (10 g, 61 mmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA), potassium phosphate tribasic (6.6 mL, 81 mmol) (granular) and tetrakis(triphenylphosphine)palladium (2.3 g, 2.0 mmol). The flask was flushed with nitrogen, DME was added, and the mixture was heated at 90° C. for 6 hours. The reaction mixture was diluted with EtOAc and water. The organic phase was washed with water and brine and then dried over anhydrous sodium sulfate. After filtration, the organic solvent was removed in vacuo to give a residue which was purified by chromatography to give the product as a yellow solid (5.80 g, 100%). MS ESI m/e: 289.2 (M+H)+.

Workup

  1. customThe flask was flushed with nitrogen, DME
  2. additionwas added
  3. additionThe reaction mixture was diluted with EtOAc and water
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. customthe organic solvent was removed in vacuo
  8. customto give a residue which
  9. customwas purified by chromatography

Sources & evidence

ORD record
ord-85797cf46328462090f0904f7df003b1
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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