Toluene → ar-Bromo-ar-nitrobenzenamine

Temperature

80 °C

1-Bromo-3,5-dinitrobenzene (14.77 g, 59.8 mmol) was dissolved in methanol (150 mL) and toluene (374 mL) and a solution of sodium hydrosulfide (10.06 g, 179 mmol) in water (10 mL) and methanol (150 mL) was added dropwise over a period of 60 minutes. The reaction was stirred at 80° C. for 3 hours. The reaction mixture was cooled to room temperature and then extracted 3 times with ethyl acetate. The organic layers were combined, washed with brine, dried with MgSO4, filtered, and concentrated under reduced pressure. The crude material required no further purification to yield 12.93 g (59.6 mmol, 100%) of 3-bromo-5-nitroaniline.

1. temperatureThe reaction mixture was cooled to room temperature
2. extractionextracted 3 times with ethyl acetate
3. washwashed with brine
4. dry with materialdried with MgSO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customno further purification

ORD record

ord-3bf75b8c14cb4c5786aaf046bf502f5c

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08735417B2