2-Nitrophenol → 1-Cyclopentyl-4-((4-nitrophenoxy)methyl)-2-(trifluoromethyl)benzene

Temperature

77 °C

In a 1 L flask equipped with a stirrer, thermocouple, condenser and a nitrogen inlet, was placed nitrophenol (28 g, 201 mmol) in DMA (150 mL) and potassium carbonate powder (28.7 g, 207 mmol). 4-(Chloromethyl)-1-cyclopentyl-2-(trifluoromethyl)benzene (45.4 g, 173 mmol) was added and washed in with DMA (120 mL). The reaction was heated at 80° C. (bath, internal 77° C.) overnight. The mixture was cooled and poured into ice water (1 L). The solids formed were allowed to settle with stirring for 4 h and collected by filtration. The solid collected was stirred in sodium bicarbonate solution (300 mL), filtered, washed with water, and air dried. The pale yellow residue was washed with hexanes (250 mL) and the solids were dried in vacuum oven overnight to give the title compound (41.4 g, ˜85% pure by LC). LCMS m/z=366.2 [M+H]+.

1. customIn a 1 L flask equipped with a stirrer
2. customthermocouple, condenser and a nitrogen inlet, was placed
3. washwashed in with DMA (120 mL)
4. temperatureThe mixture was cooled
5. additionpoured into ice water (1 L)
6. customThe solids formed
7. filtrationcollected by filtration
8. customThe solid collected
9. stirringwas stirred in sodium bicarbonate solution (300 mL)
10. filtrationfiltered
11. washwashed with water, and air
12. customdried
13. washThe pale yellow residue was washed with hexanes (250 mL)
14. customthe solids were dried in vacuum oven overnight

ORD record

ord-76e453d3a9f74109aa5bd0b0e95a04e6

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08580841B2