Ethanol → Benzenamine, 2-bromo-5-chloro-3-methyl-

Temperature

50 °C

2-Bromo-5-chloro-1-methyl-3-nitro-benzene (721 mg, 3.5 mmol, Example 135: step b) was dissolved into EtOH (6 mL). To this was added ammonium chloride (1.9 g, 35 mmol) dissolved into water (10 mL). The reaction was heated to 50° C., iron (9.6 mg, 0.34 mmol) was added and the reaction was then heated to 80° C. for 12 hours. The reaction mixture was filtered through celite, washed with methanol and EtOAc and the solvents were removed in vacuo. The residue was dissolved into EtOAc and washed with brine to remove salts. The organic layers were dried (MgSO4) and the solvents were removed in vacuo resulting in the title compound (595 mg, 78%) as a brown solid. 1H-NMR (CDCl3): δ 6.63–6.61 (m, 2H), 2.33 (s, 3H).

1. temperaturethe reaction was then heated to 80° C. for 12 hours
2. filtrationThe reaction mixture was filtered through celite
3. washwashed with methanol and EtOAc
4. customthe solvents were removed in vacuo
5. dissolutionThe residue was dissolved into EtOAc
6. washwashed with brine
7. customto remove salts
8. dry with materialThe organic layers were dried (MgSO4)
9. customthe solvents were removed in vacuo

ORD record

ord-e1bac93dbce14abf87be2a30c3ea54df

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07138530B2