Ethyl bromoacetate → HCID 13015739, compound

HRID 652878Notes

Reaction equation

HRID 652878 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]2[CH:13]=[CH:14][C:15]([OH:17])=[CH:16][C:11]=2[O:10][N:9]=1.[H-].[Na+].[H][H].Br[CH2:23][C:24]([O:26]CC)=[O:25].[OH-].[Na+]>CN(C=O)C.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]2[CH:13]=[CH:14][C:15]([O:17][CH2:23][C:24]([OH:26])=[O:25])=[CH:16][C:11]=2[O:10][N:9]=1

Participants

8

Reactant 5

HCID 7748Ethyl bromoacetateHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 135589657HCID 135589657, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13015739HCID 13015739, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Conditions

Temperature
50 °C

Procedure

3-(2-fluorophenyl)-6-hydroxy-1,2-benzisoxazole (9.7 g) is dissolved in 80 ml of DMF and added to an ice-cooled suspension of NaH (1.4 g) in 50 ml of DMF. When hydrogen evolution stops, ethyl bromoacetate (7.5 g) in 20 ml of DMF is added and the reaction mixture is allowed to come to room temperature. After two hours 200 ml of H2O and 10 ml of 50% NaOH are added and the reaction warmed at 50° C. After an additional 30 minutes a product is collected after acidification and filtering. Recrystallization from toluene/CH3CN gives {[3-(2-fluorophenyl)-1,2-benzisoxazol-6-yl]oxy}acetic acid, mp 182°-184° C.

Workup

  1. temperaturecooled
  2. customto come to room temperature
  3. customAfter an additional 30 minutes a product is collected after acidification
  4. filtrationfiltering
  5. customRecrystallization from toluene/CH3CN

Sources & evidence

ORD record
ord-5b7f57a5a0a94081bb738ec17ea30c1e
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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