Cesium carbonate → 2,3,5,6-Tetrafluoro-4'-formyl-biphenyl-4-carboxylic acid methyl ester

HRID 1470661Notes

Reaction equation

HRID 1470661 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][O:8][C:9](=[O:21])[C:10]1[C:15]([F:16])=[C:14]([F:17])[C:13](Br)=[C:12]([F:19])[C:11]=1[F:20].B(O)(O)[C:23]1[CH:28]=[CH:27][C:26]([CH:29]=[O:30])=[CH:25][CH:24]=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:7][O:8][C:9]([C:10]1[C:15]([F:16])=[C:14]([F:17])[C:13]([C:23]2[CH:28]=[CH:27][C:26]([CH:29]=[O:30])=[CH:25][CH:24]=2)=[C:12]([F:19])[C:11]=1[F:20])=[O:21]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 5910734-Formylphenylboronic AcidHCID 46311226Methyl 4-bromo-2,3,5,6-tetrafluorobenzoate

Product 1

HCID 580739392,3,5,6-Tetrafluoro-4'-formyl-biphenyl-4-carboxylic acid methyl esterYield 55.24%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

A toluene/Water (175 mL+25 mL) mixture was degassed with nitrogen for 30 minutes. Cesium carbonate (14.9 g, 43.55 mmol) was added followed by 4-bromo-2,3,5,6-tetrafluoro-benzoic acid methyl ester (5.0 g, 17.42 mmol), 4-formyl boronic acid (3.4 g, 22.64 mmol) and dichlorobis(triphenylphosphine)-palladium(II) catalyst (0.611 g, 0.87 mmol). The reaction mixture was refluxed for 15 h. TLC shows completion of the reaction. The reaction mixture was cooled to room temperature and was extracted with ethyl acetate. The combined organic layers were dried over sodium sulphate and concentrated. The obtained residue was purified by column chromatography using 5% ethyl acetate in hexane to get colorless solid (3.0 g, 55.24%).

Workup

  1. customA toluene/Water (175 mL+25 mL) mixture was degassed with nitrogen for 30 minutes
  2. temperatureThe reaction mixture was refluxed for 15 h
  3. customcompletion of the reaction
  4. extractionwas extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulphate
  6. concentrationconcentrated
  7. customThe obtained residue was purified by column chromatography

Sources & evidence

ORD record
ord-c128b4fd1700418fba75ea49be6e0733
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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