Phenethyl bromide → HCID 67196856, compound
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][NH:7][N:6]=1)=[O:4].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])=[O:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
430 mg (2.5 mM) of 4-nitro-1H-pyrazole-3-carboxylic acid methyl ester was dissolved in 4 ml of N,N-dimethylformamide, to which 0.41 ml (3 mM) of (2-bromoethyl)benzene and 1.6 g (5.0 mM) of cesium carbonate were added dropwise, and the resulting mixture was stirred under a nitrogen atmosphere for a day. The solvent was distilled off under reduced pressure, and the resultant was extracted with ethyl acetate and brine. The organic solvent layer was dried over anhydrous sodium sulfate, filtered, and then distilled under reduced pressure. The resulting impure compound was purified by column chromatography (hexane:ethyl acetate=5:1), to obtain 218 mg (31.2%) of the title compound and 506 mg (65.5%) of the compound of Preparative Example 1.
Workup
- additionwere added dropwise
- distillationThe solvent was distilled off under reduced pressure
- extractionthe resultant was extracted with ethyl acetate and brine
- dry with materialThe organic solvent layer was dried over anhydrous sodium sulfate
- filtrationfiltered
- distillationdistilled under reduced pressure
- customThe resulting impure compound was purified by column chromatography (hexane:ethyl acetate=5:1)
Sources & evidence
- ORD record
- ord-2ac6b3c378d6447c92b8f96d9b7f6aeb
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07939550B2
Reaction notes
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