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

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.

1. temperaturecooled to 0° C.
2. customquenched by slow addition of 10 ml of 5 N hydrochloric acid
3. stirringAfter stirring for 10 min
4. filtrationthe silica gel was filtered off
5. concentrationthe filtrate was concentrated to dryness under reduced pressure
6. dissolutionThe residue was dissolved in 150 ml of DCM
7. washthe solution washed with water (75 ml) and brine (75 ml)
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. customevaporated to dryness

ORD record

ord-e2770a01e9d54c43b748e73dcc3e802b

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08415336B2