2-bromo-5-tert-butylaniline

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 100-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 1-bromo-4-tert-butyl-2-nitrobenzene (2.1 g, 8.14 mmol, 1.00 equiv), sodium hyposulfite (6.6 g, 37.91 mmol, 3.50 equiv) and a solution of 2-methoxyethan-1-ol (12 mL) in water (12 mL). The resulting solution was stirred overnight at 130° C. Water (11 ml) and concentrated hydrochloric acid (11 ml) were added to the warm solution. After heated under reflux for 30 min, the reaction mixture was poured into ice water (25 ml), adjusted the pH value of the solution to 8-9 with sodium carbonate(s) and extracted with ether (3×50 mL). The combined organic layers were washed with brine and dried over anhydrous sodium sulfate. Filtration and concentration under reduced pressure gave the title compound, which was used directly for next step without further purification as a yellow liquid. 1H-NMR(400 MHz, DMSO-d6): δ ppm 1.298(s, 9H), 4.097(s, 2H), 6.682(dd, J=2 Hz, J=8.4 Hz, 1H), 6.827(d, J=2.4 Hz, 1H), 7.33(d, J=8.4 Hz, 1H). Into a 100-mL round-bottom flask purged maintained with an inert atmosphere of nitrogen After heated under reflux for 30 min extracted with ether (3×50 mL) The combined organic layers were washed with brine dried over anhydrous sodium sulfate Filtration and concentration under reduced pressure