Hydrochloric Acid → 2-Bromo-5-methylaniline

3-Nitro-4-bromotoluene (54 g) (ex Lancaster) in a water, ethanol solution (100 ml. 1:1) was rapidly stirred and iron powder (84 g) (ex BDH) was added at 25°. This mixture was heated to reflux and concentrated hydrochloric acid (2.19 g) in water, ethanol (50 ml, 1:1) was added dropwise over 30 minutes. After 4 hours at reflux, the mixture was cooled, made alkaline with 15% potassium hydroxide solution and filtered through celite washing with ethanol (2×50 ml). The resulting mixture was diluted with water (1000 ml) and worked up in the usual manner, to give 3-amino-4-bromotoluene (43.6 g). NMR 1H : 7.25(1H,d), 6.40(2H,m), 3.96(2H,bs), 2.2(3H,s).

1. temperatureThis mixture was heated
2. temperatureto reflux
3. temperatureAfter 4 hours at reflux
4. temperaturethe mixture was cooled
5. filtrationfiltered
6. washthrough celite washing with ethanol (2×50 ml)
7. additionThe resulting mixture was diluted with water (1000 ml)

ORD record

ord-e6b5c47e8db2487894f843697c7d49aa

Source dataset

uspto-grants-1993_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05202356