1-BroMo-4-isopropyl-2-nitrobenzene synthesis

Yield:204850-14-6 84%

Reaction Conditions:

with nitric acid in water at 5 - 10; for 2 h;

Steps:

91.91A

To fuming nitric acid (5 mL) cooled to 5° was added neat 4-bromoisopropylbenzene(1.0 g, 5.023 mmol) dropwise at such a rate that the reaction temperature remained below 10°. The reaction was stirred for 2 hours at 5-10°, quenched with ice (50 g), extracted with ethyl acetate (50 mL), and the organic extract was washed with water (2x25 mL) and brine (25 mL), then dried over magnesium sulfate. filtered and concentrated by rotary evaporation. The residue was purified by silica gel flash chromatography eluting with 5:95 ethyl acetate/hexanes to afford the title compound as a light yellow solid (1.03 g, 4.22 mmol, 84%). ¹H NMR (300 MHz, CHLOROFORM-D) δ ppml.27 (d, J=6.99 Hz, 6 H) 2.75 - 3.23 (m, 1 H) 7.29 (dd, J=8.82, 2.21 Hz, 1 H) 7.63 (d, J=8.09 Hz, 1 H) 7.69 (d, J=2.21 Hz, 1 H); MS (DCI) m/z 261/263 (M+NH₄)⁺.

References:

WO2008/133753,2008,A2 Location in patent:Page/Page column 129