Ammonium Chloride → 5-Bromo-4-fluoro-2-methylaniline

Temperature

100 °C

A mixture of iron powder (4.30 g) and ammonium chloride (1.143 g) in water (23 mL) was heated under reflux at 100° C. for 30 minutes. To this hot mixture was added 1-bromo-2-fluoro-4-methyl-5-nitrobenzene (5.00 g) slowly and then the reaction mixture was heated under reflux at 100° C. overnight. The mixture was cooled to room temperature, filtered through a pad of celite, and extracted with ethyl acetate (3×50 mL). The organic solution was washed with water (3×100 mL) and brine (100 mL), dried (MgSO4) and concentrated under reduced pressure to give the subtitle compound (3.59 g) as a solid. 1H NMR δ (CDCl3) 6.86-6.79 (m, 2H), 3.49 (s, 2H), 2.11 (s, 3H)

1. temperaturewas heated
2. temperaturethe reaction mixture was heated
3. temperatureunder reflux at 100° C. overnight
4. temperatureThe mixture was cooled to room temperature
5. filtrationfiltered through a pad of celite
6. extractionextracted with ethyl acetate (3×50 mL)
7. washThe organic solution was washed with water (3×100 mL) and brine (100 mL)
8. dry with materialdried (MgSO4)
9. concentrationconcentrated under reduced pressure

ORD record

ord-cf4a5f356f0548be8d969ca2f6efbf4f

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299246B2