Water → Methyl 4-(MethoxyMethyl)benzoate

Temperature

100 °C

To a mixture of methyl 4-bromobenzoate (50 mg, 0.233 mmol) and 1,4-dioxane (1 ml) were added water (0.1 ml), cesium carbonate (228 mg, 0.7 mmol), potassium methoxymethyl trifluoroborate (71 mg, 0.467 mmol) and 1′,1′-bis(diphenylphosphino)ferrocenedichloropalladium (II) (17 mg, 0.023 mmol). Then, the reaction mixture was stirred at 100° C. (external temperature) for 4.5 hours. After the reaction mixture was cooled at room temperature, water and methylene chloride were added to the mixture, followed by filtration using celite. The separated organic layer was washed with an aqueous saturated sodium chloride solution. The organic layer was separated, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethylacetate=10:1) to obtain the title compound (13.9 mg, 33%).

1. temperatureAfter the reaction mixture was cooled at room temperature
2. filtrationfollowed by filtration
3. washThe separated organic layer was washed with an aqueous saturated sodium chloride solution
4. customThe organic layer was separated
5. distillationthe solvent was distilled off under reduced pressure
6. customThe residue was purified by silica gel column chromatography (heptane:ethylacetate=10:1)

ORD record

ord-69d8474e47a540a0b4942a483dd61cf0

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07696347B2