Hydrochloric Acid → 2-Bromo-5-tert-butylaniline

Temperature

130 °C

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).

1. customInto a 100-mL round-bottom flask purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. temperatureAfter heated
4. temperatureunder reflux for 30 min
5. extractionextracted with ether (3×50 mL)
6. washThe combined organic layers were washed with brine
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationFiltration and concentration under reduced pressure

ORD record

ord-27bc2d549ca6486d8a3082d60d3f2663

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09221809B2