Sodium Carbonate → 2-Cyclopropyl-4'-fluoro-5-methoxybiphenyl-4-carbaldehyde

Temperature

100 °C

2-Bromo-4′-fluoro-5-methoxybiphenyl-4-carbaldehyde (20.6 g), cyclopropylboronic acid (10.3 g), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (4.10 g), tris(dibenzylideneacetone)dipalladium(0) (4.27 g), and a 2 M aqueous sodium carbonate solution (100 mL) were added to toluene (250 mL) in an argon atmosphere, and the mixture was stirred at 100° C. for 2 hours. The reaction mixture was allowed to cool to room temperature and poured to water, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was passed through a short silica gel column (hexane/ethyl acetate), and then, the filtrate was concentrated. The residue was crystallized from a mixed solution of ethanol (50 mL) and water (10 mL), and the obtained crystals were washed with ethanol (85 mL) to obtain the title compound (9.70 g).

1. temperatureto cool to room temperature
2. extractionfollowed by extraction with ethyl acetate
3. washThe obtained organic layer was washed with saturated saline
4. dry with materialdried over anhydrous magnesium sulfate
5. distillationthe solvent was distilled off under reduced pressure
6. concentrationthe filtrate was concentrated
7. customThe residue was crystallized from a mixed solution of ethanol (50 mL) and water (10 mL)
8. washthe obtained crystals were washed with ethanol (85 mL)

ORD record

ord-01cbbd1ea6f3462ebf5ee84cf76a9f36

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09353108B2