Ethyl bromoacetate → HCID 13015695, compound

HRID 652876Notes

Reaction equation

HRID 652876 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][N:8]=[C:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[C:6]=2[CH:5]=[CH:4][C:3]=1[OH:17].[H-].[Na+].[H][H].Br[CH2:23][C:24]([O:26]CC)=[O:25].[OH-].[Na+]>CN(C=O)C.O>[Cl:1][C:2]1[C:10]2[O:9][N:8]=[C:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[C:6]=2[CH:5]=[CH:4][C:3]=1[O:17][CH2:23][C:24]([OH:26])=[O:25]

Participants

8

Reactant 5

HCID 7748Ethyl bromoacetateHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 135589642HCID 135589642, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13015695HCID 13015695, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
65 °C

Procedure

7-chloro-6-hydroxy-3-(2-pyridyl)-1,2-benzisoxazole (10.0 g) is dissolved in 80 ml of DMF and added to an ice cold suspension of NaH (1.1 g) in 50 ml of DMF. When hydrogen evolution ceases, ethyl bromoacetate (7.5 g) in 20 ml of DMF is added. After an additional 90 minutes, 200 ml of H2O and 10 ml of 50% NaOH are added and the reaction warmed at 65° C. for 45 minutes. The mixture is poured into H2O, acidified to pH 1-2, and a solid product filtered and dried to give {[7-chloro-3-(2-pyridyl)-1,2-benzisoxazole-6-yl]oxy}acetic acid, mp 255°-256° C.

Workup

  1. filtrationa solid product filtered
  2. customdried

Sources & evidence

ORD record
ord-aa15421d5976420e8a5457fe14cfde33
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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