Hydrochloric Acid → {[7-Chloro-3-(4-fluorophenyl)-1,2-benzisoxazol-6-yl]oxy}acetic acid
Reaction equation
[H-].[Na+].Cl[C:4]1[C:19]([Cl:20])=[C:18]([OH:21])[CH:17]=[CH:16][C:5]=1[C:6](=[N:14][OH:15])[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.N#N.Br[CH2:25][C:26]([O:28]CC)=[O:27].[OH-].[Na+].Cl>CN(C=O)C.O>[Cl:20][C:19]1[C:4]2[O:15][N:14]=[C:6]([C:7]3[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=3)[C:5]=2[CH:16]=[CH:17][C:18]=1[O:21][CH2:25][C:26]([OH:28])=[O:27]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 96 °C
Procedure
To a mixture of 4.0 g NaH in 50 ml DMF, a solution of 20 g of 2,3-dichloro-4-hydroxy-4'-fluorobenzophenone oxime in 100 ml of DMF is added dropwise in an atmosphere of N2. The reaction mixture is heated to an internal temperature of 96° C. for 2 hours. The reaction mixture is cooled to 40° C. and 12.3 g of ethyl bromoacetate is added dropwise and the mixture is stirred for one hour. Twenty milliliters of 50% NaOH and 100 ml of water is added and the reaction is heated at 80°-90° C. for one hour. Concentrated HCl is added until the reaction mixture is acidic and the mixture is stirred for one half hour and water added. A solid product is collected by filtration and recrystallized to give a pure product of {[7-chloro-3-(4-fluorophenyl)-1,2-benzisoxazol-6-yl]oxy}acetic acid, mp 233°-237° C.
Workup
- temperatureThe reaction mixture is cooled to 40° C.
- temperaturethe reaction is heated at 80°-90° C. for one hour
- stirringthe mixture is stirred for one half hour
- filtrationA solid product is collected by filtration
- customrecrystallized
Sources & evidence
- ORD record
- ord-811013195f874cd6b205d17b192d413d
- Source dataset
- uspto-grants-1988_03
- Patent number
- US04728662
Reaction notes
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