Water → 4-Chloro-5-(cyclopentyloxy)-2-fluorobenzenamine
Reaction equation
[NH2:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([Cl:9])=[C:6]([OH:8])[CH:7]=1.CS(O[CH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)(=O)=O.[OH-].[Na+].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Cl:9][C:5]1[C:6]([O:8][CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:7][C:2]([NH2:1])=[C:3]([F:10])[CH:4]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
A three-necked flask (500 cc) equipped with a mechanical stirrer was charged with 5-amino-2-chloro-4-fluorophenol (10.0 g, 61.9 mmol), cyclopentyl methanesulfonate (10.3 g, 62.9 mmol) and tetrabutylammonium bromide (0.51 g, 1.58 mmol) to prepare a solution in toluene (50 mL). Subsequently, 48% sodium hydroxide in aqueous solution (30 mL) was added slowly and the mixture was stirred under heating at 80° C. for 2 h. After completion of the reaction, the reaction mixture was cooled to room temperature and water (150 mL) was added, followed by extraction with toluene (50 mL×2). The organic layers were combined, washed with water (100 mL×2) and placed under vacuum to distil off the solvent, thereby giving 4-chloro-5-cyclopentyloxy-2-fluoroaniline (13.5 g, 59.0 mmol; yield=95.2%; purity on HPLC=98.6%).
Workup
- customA three-necked flask (500 cc) equipped with a mechanical stirrer
- customAfter completion of the reaction
- temperaturethe reaction mixture was cooled to room temperature
- extractionfollowed by extraction with toluene (50 mL×2)
- washwashed with water (100 mL×2)
- customto distil off the solvent
Sources & evidence
- ORD record
- ord-1feea2015749444f961029cf4f3834c2
- Source dataset
- uspto-grants-1997_06
- Patent number
- US05639915
Reaction notes
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