Tert-Butylamine → 4-bromo-N-(tert-butyl)-2-nitroaniline

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Reaction Steps

To a solution of t-butylamine (1.3 mL, 13 mmol) in DMSO (15 mL) was added sodium hydride (60% wt. in mineral oil, 0.53 g, 14 mmol) at RT. After the reaction mixture was stirred for 10 min, it was treated with 1-bromo-4-fluoro-3-nitrobenzene (2.0 mL, 9.1 mmol). The reaction mixture was stirred at RT for 1 h the 70° C. for 3 h. After cooling to RT, it was quenched with 50 mL of water and extracted with DCM (3×40 mL). The combined organic phases were washed with 2 N HCl followed by brine. The resulting organic solution was then dried over magnesium sulfate and concentrated under reduced pressure to give 4-bromo-N-tert-butyl-2-nitrobenzenamine as a red crystalline solid. The crude product was used without further purification. MS (ESI, pos. ion) m/z: 273.9 (M+1).

Provenance & Evidence