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Sodium Methoxide → 5-Bromo-4-methoxy-6-(trifluoromethyl)pyrimidine

HRID 1172127
Notes
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Reaction equation

HRID 1172127 reaction equation
[CH3:1][O-:2].[Na+].[Br:4][C:5]1[C:6](Cl)=[N:7][CH:8]=[N:9][C:10]=1[C:11]([F:14])([F:13])[F:12]>CO>[Br:4][C:5]1[C:6]([O:2][CH3:1])=[N:7][CH:8]=[N:9][C:10]=1[C:11]([F:14])([F:13])[F:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 115362505-Bromo-4-chloro-6-(trifluoromethyl)pyrimidine

Product 1

HCID 178628975-Bromo-4-methoxy-6-(trifluoromethyl)pyrimidineYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

16.7 ml of sodium methoxide (a 28% methanol solution, 86.4 mmoles) was added, at room temperature, to a solution of 21.5 g (82.2 mmoles) of 5-bromo-4-chloro-6-trifluoromethylpyrimidine dissolved in 100 ml of methanol. The mixture was stirred to give rise to a reaction. After confirmation of the completion of the reaction, the reaction mixture was subjected to vacuum distillation to remove the solvent contained therein. The residue was poured into water, followed by extraction with chloroform. The resulting organic layer was washed with water and an aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein. The residue was washed with n-hexane to obtain 19.2 g (yield: 91.0%) of 5-bromo-4-methoxy-6-trifluoromethylpyrimidine.

Workup

  1. customto give rise
  2. customto a reaction
  3. customAfter confirmation of the completion of the reaction
  4. distillationthe reaction mixture was subjected to vacuum distillation
  5. customto remove the solvent
  6. additionThe residue was poured into water
  7. extractionfollowed by extraction with chloroform
  8. washThe resulting organic layer was washed with water
  9. dry with materialan aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate
  10. distillationThe resulting solution was subjected to vacuum distillation
  11. customto remove the solvent
  12. washThe residue was washed with n-hexane

Sources & evidence

ORD record
ord-17ea03595a7e48f486280e64c7f6cf97
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07833939B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes