Bromine → HCID 19877167, compound

HRID 1886145Notes

Reaction equation

HRID 1886145 reaction equation
[Br:1]Br.[F:3][C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([F:14])[C:5]=1[N:15]1[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[N:17]=[CH:16]1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[F:3][C:4]1[CH:9]=[C:8]([C:10]([F:12])([F:11])[F:13])[CH:7]=[C:6]([F:14])[C:5]=1[N:15]1[C:20](=[O:21])[C:19]([Br:1])=[C:18]([C:22]([F:24])([F:25])[F:23])[N:17]=[CH:16]1

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 19877157HCID 19877157, compound

Product 1

HCID 19877167HCID 19877167, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of bromine (146 mg) in acetic acid (1 ml) was added dropwise to a solution of compound 11 (in Table I) (285 mg) and sodium acetate (204 mg) in acetic acid (3 ml). After stirring at the ambient temperature for 16 hours, the solvent was removed by evaporation under reduced pressure and the residue dissolved in aqueous sodium bicarbonate solution. After extraction with ethyl acetate, the organic layer was washed with aqueous sodium thiosulphate solution, dried and filtered, and concentrated under reduced pressure to qive a pale yellow solid. Recrystallization from a mixture of ethyl acetate and petroleum ether (boiling range 60°-80° C.) gave 1-(2,6-difluoro-4-trifluoromethylphenyl)-5-bromo-4-trifluoromethylpyrimidin-6-one;

Workup

  1. customthe solvent was removed by evaporation under reduced pressure
  2. dissolutionthe residue dissolved in aqueous sodium bicarbonate solution
  3. extractionAfter extraction with ethyl acetate
  4. washthe organic layer was washed with aqueous sodium thiosulphate solution
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customRecrystallization
  9. additionfrom a mixture of ethyl acetate and petroleum ether (boiling range 60°-80° C.)

Sources & evidence

ORD record
ord-ee8e0b8a72364545a9f44f8cac0d5f2b
Source dataset
uspto-grants-1992_09
Patent number
US05149810

Reaction notes

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