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

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Reaction Conditions

Reaction Steps

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.

Provenance & Evidence