Sodium ethoxide → 5-Bromo-4-ethoxy-6-trifluoromethylpyrimidine
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
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- customto give rise
- customto a reaction
- customAfter confirmation of the completion of the reaction
- distillationthe reaction mixture was subjected to vacuum distillation
- customto remove the solvent
- additionThe residue was poured into water
- extractionfollowed by extraction with chloroform
- washThe resulting organic layer was washed with water
- dry with materialan aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate
- distillationThe resulting solution was subjected to vacuum distillation
- customto remove the solvent
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-829ec265b3b64f82b85d06e2dbb8bb8d
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07238689B2
Reaction notes
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