Ethyl bromoacetate → HCID 14012493, compound

HRID 568628Notes

Reaction equation

HRID 568628 reaction equation
[Cl:1][C:2]1[C:3]([OH:18])=[CH:4][C:5]2[O:9][N:8]=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[F:16])[C:6]=2[CH:17]=1.[H-].[Na+].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>CN(C=O)C>[Cl:1][C:2]1[C:3]([O:18][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:4][C:5]2[O:9][N:8]=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[F:16])[C:6]=2[CH:17]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetate2×HCID 24758Sodium hydride2×HCID 135991845HCID 135991845, compound

Product 1

HCID 14012493HCID 14012493, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent4×

Procedure

A solution of 5-chloro-3-(2-fluorophenyl)-6-hydroxy-1,2-benzisoxazole (14.8 g) in DMF (40 ml) is added dropwise to room temperature to a suspension of sodium hydride (3.0 g) in DMF (40 ml) and the mixture is stirred at room temperature for one half hour. A solution of ethyl bromoacetate (10.31 g) in DMF (40 ml) is then added dropwise and the mixture stirred 18 hours at room temperature. An additional 0.3 g of NaH suspended in DMF is added, followed by 1 g of ethyl bromoacetate. The mixture is warmed to 50° C. for 1 and one half hours, cooled and poured over ice/water and extracted with ether. The ether extracts are washed with water, saturated sodium chloride, dried over sodium sulfate and the solvent is removed to give a solid. Trituration with ether-petroleum ether (1:1) gives ethyl {[5-chloro-3-(2-fluorophenyl)-1,2-benzisoxazol-6-yl]oxy}acetate, mp 114°-115° C.

Workup

  1. stirringthe mixture stirred 18 hours at room temperature
  2. additionis added
  3. temperatureThe mixture is warmed to 50° C. for 1 and one half hours
  4. temperaturecooled
  5. extractionextracted with ether
  6. washThe ether extracts are washed with water, saturated sodium chloride
  7. dry with materialdried over sodium sulfate
  8. customthe solvent is removed
  9. customto give a solid

Sources & evidence

ORD record
ord-23d2d8a0e9e347ca9f8dd41e85544e11
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Reaction notes

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