Ethyl bromoacetate → HCID 13669835, compound

HRID 543399Notes

Reaction equation

HRID 543399 reaction equation
[Cl:1][C:2]1[C:15]2[O:14][C:13]3[C:8](=[C:9]([Cl:16])[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][C:3]=1[OH:18].C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][C:27]([O:29]CC)=[O:28].[OH-].[Na+]>O.CN(C=O)C>[Cl:1][C:2]1[C:15]2[O:14][C:13]3[C:8](=[C:9]([Cl:16])[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:18][CH2:26][C:27]([OH:29])=[O:28]

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 15617004HCID 15617004, compound

Product 1

HCID 13669835HCID 13669835, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4,8-dichloro-3-hydroxy-9-oxo-9H-xanthene (2.8 g), potassium carbonate (3.4 g), ethyl bromoacetate (4.2 g) and DMF (60 ml) was stirred at 60°-65° C. for 6.5 hours. After cooling the mixture, sodium hydroxide (4 g) and water (100 ml) were added and the solid crystal was recovered by filtration, washed with water and dried. Recrystallization from DMF gave 2.4 g of 4,8-dichloro-9-oxo-9H-xanthene-3-yloxyacetic acid. m.p. 270°-271° C. This compound showed a mass spectrum having a molecular ion peak at m/e 338.

Workup

  1. additionwere added
  2. filtrationthe solid crystal was recovered by filtration
  3. washwashed with water
  4. customdried
  5. customRecrystallization from DMF

Sources & evidence

ORD record
ord-c8fb47833e594319a8d5b27d88c74d75
Source dataset
uspto-grants-1987_04
Patent number
US04661607

Reaction notes

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