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1,3-Dibromo-5,5-dimethylhydantoin → 3'-Bromo-2,2,2-trifluoro-5'-(trifluoromethyl)acetophenone

HRID 1880245
Notes
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Reaction equation

HRID 1880245 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]([C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][CH:6]=1)=[O:4].[Br:17]N1C(C)(C)C(=O)N(Br)C1=O>C(O)(=O)C.S(=O)(=O)(O)O>[Br:17][C:7]1[CH:6]=[C:5]([C:3](=[O:4])[C:2]([F:15])([F:16])[F:1])[CH:10]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 1365592,2,2-Trifluoro-3'-(trifluoromethyl)acetophenone

Product 1

HCID 716518093'-Bromo-2,2,2-trifluoro-5'-(trifluoromethyl)acetophenone

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 5.00 g of 2,2,2-trifluoro-5′-(trifluoromethyl)acetophenone in 1 mL of acetic acid and 6 mL of concentrated sulfuric acid, 3.54 g of 1,3-dibromo-5,5-dimethylhydantoin was added and the resultant mixture was stirred at 35° C. for 3.5 hours. After the completion of the reaction, the reaction mixture was charged into 60 mL of ice water and the resultant mixture was extracted with chloroform (30 mL×2). The organic phase was washed with a saturated sodium hydrogen carbonate aqueous solution (50 mL×1) and then dehydrated and dried over saturated saline and anhydrous magnesium sulfate in this order, and the solvent was distilled off under reduced pressure. The resultant residue was dissolved in 20 mL of hexane and an insoluble substance was filtered off, followed by distilling off the solvent under reduced pressure to obtain 6.50 g of the objective substance as a yellow oily substance. This substance was used in the next process as it was without being further purified.

Workup

  1. customAfter the completion of the reaction
  2. extractionthe resultant mixture was extracted with chloroform (30 mL×2)
  3. washThe organic phase was washed with a saturated sodium hydrogen carbonate aqueous solution (50 mL×1)
  4. dry with materialdried over saturated saline and anhydrous magnesium sulfate in this order
  5. distillationthe solvent was distilled off under reduced pressure
  6. dissolutionThe resultant residue was dissolved in 20 mL of hexane
  7. filtrationan insoluble substance was filtered off
  8. distillationby distilling off the solvent under reduced pressure
  9. customto obtain 6.50 g of the objective substance as a yellow oily substance

Sources & evidence

ORD record
ord-7ae79283344f43728c40686a71797fc8
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08318757B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes