Ethyl Acetate → 5-Chloro-4'-fluorobiphenyl-2-amine
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-])=O)=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[CH:7]=1.[Cl-].[NH4+].C(OCC)(=O)C>C(O)C.[Fe]>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[C:5]([NH2:15])=[CH:4][CH:3]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
To a solution of the above 5-chloro-4′-fluoro-2-nitrobiphenyl (4.20 g, 15.7 mmol) and iron powder (2.75 g, 49.3 mmol) in ethanol (20 mL), a saturated aqueous ammonium chloride solution (aq., 8.0 mL) was added, and the mixture was stirred at 90° C. for 30 minutes. After the reaction, the reaction mixture was cooled to room temperature and ethyl acetate (30 mL) was added. After the organic phase was washed with water (30 mL), it was dried with sodium sulfate. After the filtration and concentration, the residue was purified by silica gel column chromatography (ethyl acetate/hexane, 1:20-1:3, v/v) to give the title compound (2.43 g, 11.0 mmol, 67%).
Workup
- customAfter the reaction
- temperaturethe reaction mixture was cooled to room temperature
- washAfter the organic phase was washed with water (30 mL), it
- dry with materialwas dried with sodium sulfate
- filtrationAfter the filtration and concentration
- customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane, 1:20-1:3
Sources & evidence
- ORD record
- ord-40d71a0d48274ca1b68444f92e9bd1e1
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08642640B2
Reaction notes
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