Hydrochloric Acid → HCID 135589646, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]2[C:13]([Cl:21])=[C:14]([Cl:20])[C:15]([O:18]C)=[C:16]([Cl:17])[C:11]=2[O:10][N:9]=1.Cl.N1C=CC=CC=1.Cl>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]2[C:13]([Cl:21])=[C:14]([Cl:20])[C:15]([OH:18])=[C:16]([Cl:17])[C:11]=2[O:10][N:9]=1Participants
Procedure
To 12.5 g of 3-(2-fluorophenyl)-6-methoxy-4,5,7-trichloro-1,2-benzisoxazole is added 80.0 g of pyridine hydrochloride. The mixture is immersed in an oil bath at 200° C. for thirty minutes with stirring. The melt is poured into one liter of iced-hydrochloric acid solution, stirred for thirty minutes, and the resultant precipitate collected and dried to yield 3-(2-fluorophenyl)-6-hydroxy-4,5,7-trichloro-1,2-benzisoxazole, mp 110° C. (dec). To 50 ml of dry dimethylformamide is added 12 g of 3-(2-fluorophenyl)-6-hydroxy-4,5,7-trichloro-1,2-benzisoxazole, 4.4 ml of ethyl bromoacetate and 20 g of potassium carbonate. The reaction is stirred at 70° C. for 2 hrs, filtered and solvent evaporated to afford an oil, which is stirred with 500 ml water for ten minutes and then extracted with ether/ethyl acetate. The organic extract is washed with water (2X), saturated sodium chloride solution, dried over anhydrous magnesium sulfate and filtered. Evaporation of the filtrate followed by recrystallization from 95% ethanol yields ethyl {[3-(2-fluorophenyl)-4,5,7-trichloro-1,2-benzisoxazol-6-yl]oxy}acetate, mp 140°-3° C.
Workup
- waitThe mixture is immersed in an oil bath at 200° C. for thirty minutes
- stirringstirred for thirty minutes
- customthe resultant precipitate collected
- customdried
Sources & evidence
- ORD record
- ord-7363b669c8864c6dab20460849c62039
- Source dataset
- uspto-grants-1987_06
- Patent number
- US04673746
Reaction notes
Loading…