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

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%).

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

ORD record

ord-c128b4fd1700418fba75ea49be6e0733

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09006454B2