Sodium borohydride → 1-Fluoro-2-methyl-3-(2-nitroethyl)benzene

Participants

Reaction Steps

Analogously to the procedure described in A. K. Sinhababu et al., Tetrahedron Lett. 24 (1983), 227, to a solution of the compound of step 1 (16.85 g, 93.01 mmol) in isopropanol (275 ml) and chloroform (825 ml) were added dry silica gel (110 g) and then in small portions sodium borohydride (7.038 g, 186.02 mmol). The mixture was stirred at room temperature for 0.5 h, then cooled to 0° C. and quenched by slow addition of 10 ml of 5 N hydrochloric acid. After stirring for 10 min, the silica gel was filtered off and the filtrate was concentrated to dryness under reduced pressure. The residue was dissolved in 150 ml of DCM and the solution washed with water (75 ml) and brine (75 ml), dried over magnesium sulfate, filtered and evaporated to dryness to give 15.02 g of the title compound as a thick orange oil.

Provenance & Evidence