反应详情

Under a nitrogen atmosphere, a mixture of 2-chloro-6-fluorobenzaldehyde (84) (50.0 g, 315 mmol), compound (55) (73.5 g, 347 mmol), Pd-132 (made by Johnson Matthey Catalysis and Chiral Technologies) (0.223 g, 0.315 mmol), potassium carbonate (87 g, 631 mmol) and TBAB (20.33 g, 63.1 mmol) was refluxed in a toluene 500 mL)-ethanol (100 mL)-water (500 mL) solvent for 5 hours. The reaction mixture was extracted with 300 mL of toluene three times. Combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine, and then dried over magnesium sulfate, and a solvent was distilled off by an evaporator. The residue was purified by silica gel column chromatography, and thus 4-ethoxy-3,3′-difluoro-[1,1′-biphenyl]-2,2′-dicarboaldehyde (85) (77.25 g, yield 84%) was obtained.

1. extractionThe reaction mixture was extracted with 300 mL of toluene three times
2. washCombined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine
3. dry with materialdried over magnesium sulfate
4. distillationa solvent was distilled off by an evaporator
5. customThe residue was purified by silica gel column chromatography