Water → 2',4,6'-Trifluorobiphenyl-3-carbaldehyde

Temperature

100 °C

To a solution of 2-bromo-1,3-difluorobenzene (100 g, 477.46 mmol) and 4-fluoro-3-formylphenylboronic acid (96.2 g, 572.95 mmol) in toluene (1432 mL) at RT was added Na2CO3 (2M in H2O) (477.46 mL, 954.2 mmol) and PdCl2(dppf) (7.798 g, 9.54 mmol). The reaction mixture was stirred at 100° C. for 8 h and cooled to RT. Water was added to the reaction mixture and extracted with EtOAc (2×500 mL). Organic layer was washed with brine and dried over Na2SO4. The organic layer was concentrated and purified by column using silica (100-200 mesh) and 0-5% EtOAc-hexane to provide 2′,4,6′-trifluorobiphenyl-3-carbaldehyde (54.3 g, 49.4% yield).

1. temperaturecooled to RT
2. extractionextracted with EtOAc (2×500 mL)
3. washOrganic layer was washed with brine
4. dry with materialdried over Na2SO4
5. concentrationThe organic layer was concentrated
6. custompurified by column

ORD record

ord-61e63afbe4194cf69cdf0b326bef5c55

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09090593B2