Bromine → HCID 67547686, compound

HRID 2356726Notes

Reaction equation

HRID 2356726 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:12]=2)=[CH:4][CH:3]=1.[Br:18]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[Br:18][C:10]1[O:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[N:12][C:11]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 15170579Ethyl 2-(4-fluorophenyl)-1,3-oxazole-4-carboxylate

Product 1

HCID 67547686HCID 67547686, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of ethyl 2-(4-fluorophenyl)oxazole-4-carboxylate (7.44 g) in chloroform (100 ml) was added dropwise bromine (8.1 ml) at room temperature, and the resulting mixture was stirred at room temperature for 30 minutes and then refluxed for 8 hours. After cooling the reaction mixture, 10% aqueous sodium thiosulfate solution was added to the mixture and the mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and brine, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (solvent: ethyl acetate:n-hexane=1:9) to obtain ethyl 5-bromo-2-(4-fluorophenyl)-oxazol-4-carboxylate (9.21 g) as pale yellowish powder.

Workup

  1. temperaturerefluxed for 8 hours
  2. additionwas added to the mixture
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (solvent: ethyl acetate:n-hexane=1:9)

Sources & evidence

ORD record
ord-ee54e96a22b4436a9e9c553c37a161f8
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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