Potassium Carbonate → 2-Fluoro-4-chloro-5-cyclopentyloxynitrobenzene
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC(S(O[CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)(=O)=O)=CC=1>C(#N)C>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]Participants
Procedure
A solution of 2-fluoro-4-chloro-5-hydroxynitrobenzene (7.1 g, 37.1 mmol) and potassium carbonate (5.1 g, 37.1 mmol) in acetonitrile (300 ml) was stirred for 2 hours at a refluxing temperature. Cyclopentyl p-toluenesulfonate (10.3 g, 40.8 mmol) was added thereto, followed by stirring further for 2 hours under refluxing. After completion of the reaction, the solvent was distilled off under reduced pressure from the reaction mixture, 1N hydrochloric acid (800 ml) was added thereto, and the mixture was extracted with ethyl acetate (100 ml×3 times). The organic layer was washed with an aqueous solution of sodium bicarbonate and water, dried, and the solvent was distilled off under reduced pressure to obtain 2-fluoro-4-chloro-5-cyclopentyloxynitrobenzene as a yellow solid (8.93 g, 34.3 mmol, 92.6% yield).
Workup
- temperatureunder refluxing
- customAfter completion of the reaction
- distillationthe solvent was distilled off under reduced pressure from the reaction mixture, 1N hydrochloric acid (800 ml)
- additionwas added
- extractionthe mixture was extracted with ethyl acetate (100 ml×3 times)
- washThe organic layer was washed with an aqueous solution of sodium bicarbonate and water
- customdried
- distillationthe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-e6cee3e6b5ac4c1d9fc5123fc3052065
- Source dataset
- uspto-grants-1995_11
- Patent number
- US05464811
Reaction notes
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