Ethyl bromoacetate → HCID 13015761, compound

HRID 652903Notes

Reaction equation

HRID 652903 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][N:8]=[C:7]([C:11]3[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][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]=[C:15]([F:17])[CH:14]=[CH:13][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 135589650HCID 135589650, compound

Product 1

HCID 13015761HCID 13015761, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 9.3 g of 7-chloro-3-(2,5-difluorophenyl)-6-hydroxy-1,2-benzisoxazole in 100 ml of DMF, 4.97 g of K2CO3 and 6.07 g of ethyl bromoacetate is added dropwise. The mixture is heated for two hours at 60° C. To the mixture 200 ml of water and 15 ml of 50% NaOH are added. The mixture is stirred at 90° C. for 90 minutes and then poured into water and acidified. The product is extracted with ethylacetate, dried over Na2SO4 and evaporated to give {[7-chloro-3-(2,5-difluorophenyl)-1,2-benzisoxazol-6-yl]oxy}acetic acid.

Workup

  1. extractionThe product is extracted with ethylacetate
  2. dry with materialdried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-7f2e605aec734004bbc9ff01ecde266c
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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