Dimethylformamide → HCID 14012522, compound

HRID 652928Notes

Reaction equation

HRID 652928 reaction equation
CN(C)C=O.[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[C:17]2[C:18]([Cl:25])=[C:19]([Cl:24])[C:20]([OH:23])=[C:21]([Cl:22])[C:16]=2[O:15][N:14]=1.Br[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].C(=O)([O-])[O-].[K+].[K+]>O>[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[C:17]2[C:18]([Cl:25])=[C:19]([Cl:24])[C:20]([O:23][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:21]([Cl:22])[C:16]=2[O:15][N:14]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 135589646HCID 135589646, compound

Product 1

HCID 14012522HCID 14012522, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

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

  1. filtrationfiltered
  2. customsolvent evaporated
  3. customto afford an oil, which
  4. extractionextracted with ether/ethyl acetate
  5. extractionThe organic extract
  6. washis washed with water (2X), saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customEvaporation of the filtrate
  10. customfollowed by recrystallization from 95% ethanol

Sources & evidence

ORD record
ord-e2deeb0f3838492f991ef74cd1dcbe1e
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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