Ammonium Chloride → 3-Bromo-5-(difluoromethyl)aniline
Reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([CH:11]([F:13])[F:12])[CH:3]=1.[NH4+].[Cl-]>C(O)C.O.C(OCC)(=O)C.[Fe]>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([CH:11]([F:12])[F:13])[CH:3]=1)[NH2:8]Participants
7
Conditions
- Temperature
- 95 °C
Procedure
Iron (1.99 g, 35.7 mmol) was added to a vigorously stirred mixture of 1-bromo-3-(difluoromethyl)-5-nitrobenzene (1.80 g, 7.14 mmol) and NH4Cl (0.191 g, 3.57 mmol) in ethanol (30 mL) and water (15 mL). The mixture was heated to 95° C. for 2 h. It was then diluted with ethyl acetate while still hot and filtered over Celite. The filtrate was washed with dilute aqueous NaHCO3 and brine. After solvent evaporation the residue was purified through a silica plug, eluting with 1:5 ethyl acetate:hexanes to yield 3-bromo-5-(difluoromethyl)aniline (1.3 g, 5.86 mmol, 82%).
Workup
- filtrationfiltered over Celite
- washThe filtrate was washed with dilute aqueous NaHCO3 and brine
- customAfter solvent evaporation the residue
- customwas purified through a silica plug
- washeluting with 1:5 ethyl acetate
Sources & evidence
- ORD record
- ord-815a15953f74402c92922859b5992a5e
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08759366B2
Reaction notes
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