Dimethylformamide → HCID 13669827, compound

HRID 543391Notes

Reaction equation

HRID 543391 reaction equation
[Cl:1][C:2]1[C:15]2[O:14][C:13]3[C:8](=[C:9]([F: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][CH2:30][CH3:31])=[O:28].CN(C)C=O>O>[Cl:1][C:2]1[C:15]2[O:14][C:13]3[C:8](=[C:9]([F: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]([O:29][CH2:30][CH3:31])=[O:28]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 13669826HCID 13669826, compound

Product 1

HCID 13669827HCID 13669827, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.6 g of 4-chloro-8-fluoro-3-hydroxy-9-oxo-9H-xanthene, 2.8 g of potassium carbonate, 3.3 g of ethyl bromoacetate and 40 ml of N,N-dimethylformamide (DMF) was stirred at 60°-70° C. for 4 hours. After cooling the mixture, water was added thereto and the resulting crystal was recovered by filtration, washed with water and dried. Recrystallization from ethanol gave 3.4 g of ethyl 4-chloro-8-fluoro-9-oxo-9H-xanthene-3-yloxyacetate. A mixture of this ester (3.3 g), sodium hydroxide (1.9 g) and water (100 ml) was refluxed for 30 minutes. After cooling, the mixture was rendered acidic with concentrated hydrochloric acid and the resulting crystal was recovered by filtration and dried. Recrystallization from DMF gave 2.5 g of 4-chloro-8-fluoro-9-oxo-9H-xanthene-3-yloxyacetic acid. m.p. 300° C.

Workup

  1. additionwas added
  2. filtrationthe resulting crystal was recovered by filtration
  3. washwashed with water
  4. customdried
  5. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-6f6bc954f78c41649c517f2faa7f4e66
Source dataset
uspto-grants-1987_04
Patent number
US04661607

Reaction notes

Loading…