Sodium Carbonate → Methyl 4-cyclopropyl-2-ethoxybenzoate

Temperature

100 °C

Cyclopropylboronic acid (1.90 g), a 2 M aqueous sodium carbonate solution (22 mL), tris(dibenzylideneacetone)dipalladium(0) (944 mg), and dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (907 mg) were added at room temperature to a toluene (80 mL) solution of methyl 2-ethoxy-4-iodobenzoate (4.51 g), and the mixture was stirred at 100° C. for 18 hours in an argon atmosphere. Water was added to the reaction mixture at room temperature, and the mixture was filtered through celite. Then, the filtrate was subjected to extraction with ethyl acetate. The obtained organic layer was washed with water and saturated saline in this order and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (3.25 g).

1. filtrationthe mixture was filtered through celite
2. extractionThen, the filtrate was subjected to extraction with ethyl acetate
3. washThe obtained organic layer was washed with water and saturated saline in this order
4. dry with materialdried over anhydrous magnesium sulfate
5. distillationthe solvent was distilled off under reduced pressure
6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

ORD record

ord-de80f0c04aa545a5a38e8697fb336ec8

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09353108B2