Ethyl bromoacetate → HCID 13015773, compound

HRID 652891Notes

Reaction equation

HRID 652891 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:18])=[C:16]([I:17])[C:11]=2[O:10][N:9]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:26][C:27]([O:29]CC)=[O:28].[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:18][CH2:26][C:27]([OH:29])=[O:28])=[C:16]([I:17])[C:11]=2[O:10][N:9]=1

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 135589636HCID 135589636, compound

Product 1

HCID 13015773HCID 13015773, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

3-(2-fluorophenyl)-6-hydroxy-7-iodo-1,2-benzisoxazole (7.80 g) in 80 ml of DMF is treated at 60° C. with 6.6 g of K2CO3 and 7.9 g of ethyl bromoacetate. After one hour the temperature is increased to 90° C. and 80 ml of H2O and 8 ml of 50% NaOH are added. After an additional 30 minutes the mixture is poured into H2O and acidified and then extracted into ether, dried and evaporated to yield {[3-(2-fluorophenyl)-7-iodo-1,2-benzisoxazol-6-yl]oxy}acetic acid, mp 178°-180° C.

Workup

  1. extractionextracted into ether
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-3c71883443e8430a9b7902377fa870ac
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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