Benzene, 1-bromo-3-(trifluoromethyl)- → 3-(Nitromethyl)-3-[3-(trifluoromethyl)phenyl]oxetane

Temperature

-78 °C

A solution of 103 mg of 1-bromo-3-(trifluoromethyl)benzene (0.46 mmol) in 4 ml anhydrous THF is treated slowly at −78° C. with an n-butyllithium solution (1.6 M in hexane, 312 μl, 0.50 mmol). After 15 mins' stirring at −78° C., a solution of 50 mg (0.43 mmol) of 3-nitromethylenoxetane [Herstellung: G. Wuitschik et al., Agnew. Chem. Int. Ed. 45 (46), 7736-7739 (2006)] in 2 ml THF is added. The mixture is stirred overnight at −78° C. and then the reaction is stopped by addition of 5 ml of saturated ammonium chloride solution at −78° C. After warming to RT, the mixture is diluted with water and extracted three times with dichloromethane. The combined organic phases are dried over sodium sulphate and freed of the volatile components on the rotary evaporator. The oily residue is briefly dried under high vacuum. 53 mg (33% of theory) of the title compound in ca. 70% purity are obtained.

1. stirringThe mixture is stirred overnight at −78° C.
2. temperatureAfter warming to RT
3. extractionextracted three times with dichloromethane
4. dry with materialThe combined organic phases are dried over sodium sulphate
5. customfreed of the volatile components on the rotary evaporator
6. customThe oily residue is briefly dried under high vacuum

ORD record

ord-0ac8ba07411741b6ae88e6c90769e4bd

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08084481B2