Water → 4-Chloro-5-(cyclopentyloxy)-2-fluorobenzenamine
Reaction equation
NC1C(F)=CC(Cl)=C(O[C:9](=O)[O:10][C:11]2[CH:16]=[C:15]([NH2:17])[C:14]([F:18])=[CH:13][C:12]=2[Cl:19])C=1.[CH:23]1(Br)[CH2:27]C[CH2:25][CH2:24]1.[OH-].[Na+].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Cl:19][C:12]1[C:11]([O:10][CH:9]2[CH2:25][CH2:24][CH2:23][CH2:27]2)=[CH:16][C:15]([NH2:17])=[C:14]([F:18])[CH:13]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
A round-bottomed flask (50 cc) was charged with bis(5-amino-2-chloro-4-fluorophenyl)carbonate (1.52 g, 4.36 mmol), cyclopentyl bromide (1.39 g, 9.29 mmol) and tetrabutylammonium bromide (74 mg, 0.23 mmol) to prepare a solution in toluene (12 mL). Subsequently, 48% sodium hydroxide in aqueous solution (6 mL) was added slowly and the mixture was stirred under heating at 80° C. for 1 h. After completion of the reaction, the reaction mixture was cooled to room temperature and water (15 mL) was added, followed by extraction with toluene (10 mL×2). The organic layers were combined and washed with water (10 mL×2). The solvent was distilled off under vacuum from the resulting toluene solution, thereby giving 4-chloro-5-cyclopentyloxy-2-fluoroaniline (1.93 g, 8.40 mmol; yield=96.3% ).
Workup
- customAfter completion of the reaction
- temperaturethe reaction mixture was cooled to room temperature
- extractionfollowed by extraction with toluene (10 mL×2)
- washwashed with water (10 mL×2)
- distillationThe solvent was distilled off under vacuum from the resulting toluene solution
Sources & evidence
- ORD record
- ord-bfda8d0e14dd4499b2c50ac12f9c4c6e
- Source dataset
- uspto-grants-1997_06
- Patent number
- US05639915
Reaction notes
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