Thionyl Chloride → 4-(Chloromethyl)-1-cyclopentyl-2-(trifluoromethyl)benzene

Temperature

50 °C

To (4-cyclopentyl-3-(trifluoromethyl)phenyl)methanol (1.21 g, 4.95 mmol) was added thionyl chloride (5.5 mL, 74.2 mmol). The mixture was heated at 50° C. for 2 h before it was allowed to cool to room temperature and stirred at room temperature overnight. The mixture was poured into ice and stirred for 5 min before it was extracted with dichloromethane. The organic extract was washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound as an oil (1.16 g). 1H NMR (400 MHz, CDCl3) δ ppm 1.55-1.63 (m, 2H), 1.69-1.77 (m, 2H), 1.82-1.90 (m, 2H), 2.05-2.13 (m, 2H), 3.37 (quintet, J=8.59 Hz, 1H), 4.58 (s, 2H), 7.46 (d, J=8.00 Hz, 1H), 7.52 (d, J=8.00 Hz, 1H), 7.61 (d, J=1.52 Hz, 1H).

1. temperatureto cool to room temperature
2. additionThe mixture was poured into ice
3. stirringstirred for 5 min before it
4. extractionwas extracted with dichloromethane
5. extractionThe organic extract
6. washwas washed with saturated aqueous sodium bicarbonate solution
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated under reduced pressure

ORD record

ord-27e87bb85e8345b4ba4a8ff8d7e095e2

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09175320B2