Potassium Carbonate → Dimethyl 2',5'-difluoro-1,1'-biphenyl-2,4-dicarboxylate

HRID 1662545Notes

Reaction equation

HRID 1662545 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][C:8]=1[C:17]([O:19][CH3:20])=[O:18])(=O)=O.[F:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cl-].[Na+].O.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>[F:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[C:7]1[C:8]([C:17]([O:19][CH3:20])=[O:18])=[CH:9][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:15][CH:16]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2734335(2,5-Difluorophenyl)boronic acidHCID 120175464-[[(Trifluoromethyl)sulfonyl]oxy]-1,3-benzenedicarboxylic acid dimethyl ester

Product 1

HCID 57707138Dimethyl 2',5'-difluoro-1,1'-biphenyl-2,4-dicarboxylateYield 90.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of dimethyl 4-(trifluoromethylsulfonyloxy)isophthalate 66.13B (1.00 g, 2.9 mmol) in DMF (5.8 mL) at 23° C. was added 2,5-difluorophenylboronic acid (0.69 g, 4.4 mmol) (commercially available from Aldrich), and potassium carbonate (1.2 g, 8.8 mmol). Tetrakis(triphenylphosphine)palladium (0.24 g, 0.20 mmol) was then added to the mixture. The mixture was heated to 90° C. and was stirred for 17 hours. The reaction was then cooled to room temperature, diluted with brine and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-10% EtOAc in hexanes) to yield 83.27A as a colorless oil (0.800 g, 89% yield).

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. extractionextracted three times with EtOAc
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. filtrationfiltering
  5. customthe organic solvent was removed under reduced pressure
  6. customthe product was then purified on silica gel (0-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-696275f4ae994c9ea96b7db3a8e45ccb
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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