Ethyl bromoacetate → HCID 13669835, compound

HRID 1194847Notes

Reaction equation

HRID 1194847 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-8b9855df3a9b4919a219ba7ecee89ad2
Source dataset
uspto-grants-1989_03
Patent number
US04816479

Reaction notes

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