Acetic Acid → 3-Bromo-4-methoxy-6-(trifluoromethyl)pyridazine
Reaction equation
[Br:1][C:2]1[N:3]=[N:4][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:6][C:7]=1Br.C[O-].[Na+].[C:16](O)(=[O:18])C>CO>[Br:1][C:2]1[N:3]=[N:4][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:6][C:7]=1[O:18][CH3:16]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of 3,4-dibromo-6-trifluoromethyl-pyridazine (D5) (1.48 g, 4.85 mmol) in methanol at 0° C., was added a 30% solution of sodium methoxide in methanol (0.8 ml, 4.67 mol). The reaction mixture was stirred at 0° C. for 1 h. After this period, the reaction mixture was neutralized by acetic acid addition and the solvent evaporated in vacuo. The crude product was purified by flash column chromatography (silica gel; 3% ammonia in methanol (7M)/dichloromethane). The desired fractions were collected and evaporated in vacuo. to yield D6 (0.79 g, 64%) as a solid. C6H4BrF3N2O requires 257; Found 258 (MH+).
Workup
- waitAfter this period
- customthe solvent evaporated in vacuo
- customThe crude product was purified by flash column chromatography (silica gel; 3% ammonia in methanol (7M)/dichloromethane)
- customThe desired fractions were collected
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-09929adc8f6140d7bfea5245b561fca6
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08906921B2
Reaction notes
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