Hydrochloric Acid → 2-Bromo-5-methoxyaniline

4-Bromo-3-nitroanisole (19.8 g, 85.1 mmol) was dissolved in methanol (150 ml). Conc. HCl (40 ml) was added to the resultant solution, and the mixture was stirred while cooling. During stirring, reduced iron (14.3 g) was added to the mixture by small portions, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was condensed under reduced pressure. 2N-Caustic soda solution (100 ml) was added to the condensate, and the insoluble matter was filtered off. The filtrate was extracted with chloroform. The organic phase was dried and condensed under reduced pressure to obtain 16.0 g of the title compound, 3-methoxyaniline, as a brown oil (93.0%).

1. temperaturewhile cooling
2. stirringDuring stirring
3. stirringthe mixture was stirred at room temperature for 4 hours
4. customcondensed under reduced pressure
5. filtrationthe insoluble matter was filtered off
6. extractionThe filtrate was extracted with chloroform
7. customThe organic phase was dried
8. customcondensed under reduced pressure

ORD record

ord-0a6dff239dcd4928b1e937a071b2de82

Source dataset

uspto-grants-1996_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05576324