Bromine → HCID 19877167, compound

HRID 1461734Notes

Reaction equation

HRID 1461734 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 agueous sodium bicarbonate solution. After extraction with ethyl acetate, the organic layer was washed with agueous sodium thiosulphate solution, dried and filtered, and concentrated under reduced pressure to give 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 agueous sodium bicarbonate solution
  3. extractionAfter extraction with ethyl acetate
  4. washthe organic layer was washed with agueous sodium thiosulphate solution
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a pale yellow solid
  9. customRecrystallization
  10. additionfrom a mixture of ethyl acetate and petroleum ether (boiling range 60°-80° C.)

Sources & evidence

ORD record
ord-8f8c6d25d37e498895ab9802cc521962
Source dataset
uspto-grants-1991_12
Patent number
US05077297

Reaction notes

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