Water → HCID 14012506, compound

HRID 568679Notes

Reaction equation

HRID 568679 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:5]([OH:21])=[C:6]([Cl:20])[C:7]2[O:11][N:10]=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[F:18])[C:8]=2[CH:19]=1.Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].O>CN(C=O)C>[CH2:27]([O:26][C:24](=[O:25])[CH2:23][O:21][C:5]1[C:4]([Cl:3])=[CH:19][C:8]2[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[F:18])=[N:10][O:11][C:7]=2[C:6]=1[Cl:20])[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 135589651HCID 135589651, compound

Product 1

HCID 14012506HCID 14012506, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
45 °C

Procedure

1.4 g NaH is suspended in 50 ml DMF with stirring. A solution of 7.2 g of 5,7-dichloro-3-(2-fluorophenyl)-6-hydroxy-1,2-benzisoxazole in 50 ml DMF is added dropwise. The solution is heated to 45° C. for one hour. Ethyl bromoacetate (4.0 g) in 20 ml DMF is added dropwise and the reaction is stirred at 40° C. for two hours. The solution is poured into 1 l of water, stirred and extracted with ethylacetate. The organic extracts are washed with saturated NaCl solution and the solvent removed in vacuo affording ethyl{[5,7-dichloro-3-(2-fluorophenyl)-1,2-benzisoxazole-6-yl]oxy}acetate, mp 105°-106° C.

Workup

  1. stirringthe reaction is stirred at 40° C. for two hours
  2. stirringstirred
  3. extractionextracted with ethylacetate
  4. washThe organic extracts are washed with saturated NaCl solution
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-5468fdf7235745e5aae314df891de9b3
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Reaction notes

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