Sodium Carbonate → 6-Cyclopropyl-3-ethoxy-2,4'-difluorobiphenyl-4-carbaldehyde

Temperature

100 °C

Cyclopropylboronic acid (1.79 g), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (854 mg), tris(dibenzylideneacetone)dipalladium (0) (953 mg) and 2M aqueous sodium carbonate solution (15.6 mL) were added to a solution of 6-bromo-3-ethoxy-2,4′-difluorobiphenyl-4-carbaldehyde (3.55 g) in toluene (35 mL) at room temperature. The mixture was stirred at 100° C. under argon atmosphere for 16 hours. The mixture was quenched with water at room temperature and filtrated through celite. The filtrate was extracted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by a silica gel column chromatography (hexane/ethyl acetate) to give the title compound (2.99 g).

1. customThe mixture was quenched with water at room temperature
2. filtrationfiltrated through celite
3. extractionThe filtrate was extracted with ethyl acetate
4. customThe organic layer was separated
5. washwashed with water and brine
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationconcentrated in vacuo
8. customThe residue was purified by a silica gel column chromatography (hexane/ethyl acetate)

ORD record

ord-420ba717b60943aa9106abaa2208b4a2

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09353108B2