Dimethylformamide → 1092496-74-6

Temperature

60 °C

Potassium carbonate (6.55 g, 47.4 mmol), cyclopentyl bromide (8.25 g, 55.3 mmol) and DMF (5 ml) were added to a DMF solution (10 ml) of 5′-bromo-2′-hydroxyacetophenone (8.5 g, 39.5 mmol), and the resulting mixture was stirred at 60° C. for 4.5 hours. Potassium carbonate (3.0 g, 21.7 mmol) and cyclopentyl bromide (2.0 g, 13.4 mmol) were added to the resultant mixture, and stirred at 60° C. for 9 hours. After the reaction mixture was cooled to room temperature, water was added, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution, and then concentrated under reduced pressure. The residue was then purified by silica gel column chromatography (n-hexane:ethyl acetate=9:1). The purified product was concentrated under reduced pressure to thereby obtain 11.3 g of oily pale yellow 1-(5-bromo-2-cyclopentyloxyphenyl)ethanone (yield: 100%).

1. stirringstirred at 60° C. for 9 hours
2. temperatureAfter the reaction mixture was cooled to room temperature
3. extractionthe resulting mixture was extracted with ethyl acetate
4. washThe organic layer was washed with a saturated sodium chloride aqueous solution
5. concentrationconcentrated under reduced pressure
6. customThe residue was then purified by silica gel column chromatography (n-hexane:ethyl acetate=9:1)
7. concentrationThe purified product was concentrated under reduced pressure

ORD record

ord-456a7f36324a4f3f9d8b21d1de6dd3a5

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08642619B2