Ethyl bromoacetate → HCID 13015760, compound

HRID 652896Notes

Reaction equation

HRID 652896 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]=[C:13]([F:17])[C:12]=3[F:18])[C:6]=2[CH:5]=[CH:4][C:3]=1[OH:19].C([O-])([O-])=O.[K+].[K+].Br[CH2:27][C:28]([O:30]CC)=[O:29].[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]=[C:13]([F:17])[C:12]=3[F:18])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:19][CH2:27][C:28]([OH:30])=[O:29]

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 135589654HCID 135589654, compound

Product 1

HCID 13015760HCID 13015760, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 12 g of 7-chloro-6-hydroxy-3-(2,3-difluorophenyl)-1,2-benzisoxazole in 120 ml of DMF, 6.36 g of K2CO3 is added followed by 7.83 g of BrCH2CO2C2H5. The reaction is warmed at 60° C. for two hours and then allowed to stand for 18 hours. To the mixture 200 ml of water and 15 ml of 50% NaOH are added. The mixture is warmed at 90° C. for 90 minutes, poured into water and acidified. The product is extracted into ethylacetate which is dried over Na2SO4 and evaporated to give {[7-chloro-3-(2,3-difluorophenyl)-1,2-benzisoxazol-6-yl]oxy}acetic acid, mp 183°-187° C.

Workup

  1. temperatureThe mixture is warmed at 90° C. for 90 minutes
  2. extractionThe product is extracted into ethylacetate which
  3. dry with materialis dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-d5e646496b564a91883341c7e5b8bf64
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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