Sodium ethoxide → 5-Bromo-4-ethoxy-6-trifluoromethylpyrimidine

HRID 1172128Notes

Reaction equation

HRID 1172128 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].[Br:5][C:6]1[C:7](Cl)=[N:8][CH:9]=[N:10][C:11]=1[C:12]([F:15])([F:14])[F:13]>C(O)C>[Br:5][C:6]1[C:7]([O:1][CH2:2][CH3:3])=[N:8][CH:9]=[N:10][C:11]=1[C:12]([F:15])([F:14])[F:13]

Participants

4

Procedure

0.94 g (13.77 mmoles) of sodium ethoxide was added, at room temperature, to a solution of 3.00 g (11.48 mmoles) of 5-bromo-4-chloro-6-trifluoromethylpyrimidine dissolved in 50 ml of ethanol. 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 purified by silica gel column chromatography to obtain 2.44 g (yield: 82.9%) of 5-bromo-4-ethoxy-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. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f3d6531967b447a2b4f512e6254f84c7
Source dataset
uspto-grants-2010_11
Patent number
US07833939B2

Reaction notes

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