Methyl iodide → HCID 15735343, compound
Reaction equation
[F:1][CH:2]([F:18])[C:3]1[N:7]([CH3:8])[N:6]=[C:5]([O:9][Si](C)(C)C(C)(C)C)[C:4]=1Br.[CH2:19]([Li])CCC.CI.F[C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[C:29]([O:36][CH3:37])[CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.C(#N)C.CS(C)=O.O.CCOCC>[F:18][CH:2]([F:1])[C:3]1[N:7]([CH3:8])[N:6]=[C:5]([O:9][C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[C:29]([O:36][CH3:37])[CH:28]=2)[C:4]=1[CH3:19]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 5
Procedure
To a solution of 15.4 g (45.16 mmol) of 5-difluoromethyl-4-bromo-3-(bismethyl-t-butylsiloxy)-1-methylpyrazole in anhydrous THF was added 18.06 ml of 2.5 molar n-butyl lithium at -78° C. The mixture was stirred for 1 hour with methyl iodide and warmed to room temperature. Ether was added and the ether layer was washed with water, dried and evaporated to give an oily residue. The residue was dissolved in 100 ml of acetonitrile and 5 ml of concentrated aqueous HF added to precipitate 2.8 g of a white solid mp 145°-146° C. (b) A mixture of 1.0 g of the product of step (a) (6.17 mmol), 4-fluoro-2-methoxynitrobenzene (1.06 g 6.17 mmol), and 0.94 g of potassium carbonate (6.79 mmol) in 50 ml dimethyl sulfoxide was heated to 80° C. for 15 hours. The reaction was then poured into 200 ml cold water and stirred for 1-2 hours. The precipitate formed was collected to give 1.8 g of a white solid product m.p. 57°-58° C.
Workup
- washthe ether layer was washed with water
- customdried
- customevaporated
- customto give an oily residue
- addition5 ml of concentrated aqueous HF added
- customto precipitate 2.8 g of a white solid mp 145°-146° C. (b)
- temperaturewas heated to 80° C. for 15 hours
- customThe precipitate formed
- customwas collected
Sources & evidence
- ORD record
- ord-bb25413072b44e99bf205dcb2518f9b8
- Source dataset
- uspto-grants-1991_09
- Patent number
- US05045106
Reaction notes
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