Chlorodifluoromethane → 3-(2,4-dichlorophenyl)-1-difluoromethyl-6-methyl-2(1H)-pyridone
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10](=[O:16])[NH:11][C:12]([CH3:15])=[CH:13][CH:14]=1.[OH-].[K+].Cl[CH:20]([F:22])[F:21]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10](=[O:16])[N:11]([CH:20]([F:22])[F:21])[C:12]([CH3:15])=[CH:13][CH:14]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
4.0 g of 3-(2,4-dichlorophenyl)-6-methyl-2(1H)-pyridone, 0.8 g of tetrabutylammonium bromide and 2.6 g of potassium hydroxide were dissolved in 100 ml of THF, and chlorodifluoromethane was blown therein under cooling to 0° C. After completion of the blowing, stirring was continued further at room temperature for 1 hour to complete the reaction. Then, the solvent was distilled off under reduced pressure, and the residue was extracted with ethyl acetate and washed with water. Then, the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off, and the obtained crude product was purified by silica gel column chromatography to obtain 0.70 (yield: 14%) of the desired product. Melting point: 83-85° C.
Workup
- customthe reaction
- distillationThen, the solvent was distilled off under reduced pressure
- extractionthe residue was extracted with ethyl acetate
- washwashed with water
- dry with materialThen, the organic layer was dried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off
- customthe obtained crude product
- customwas purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-f318612860504d06a69ac712968a510e
- Source dataset
- uspto-grants-2002_10
- Patent number
- US06472348B1
Reaction notes
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