Ethyl bromoacetate → Diethyl 3-cyano-3-(3,4-dichlorophenyl)pentanedioate
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[Cl:8].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>C1COCC1.C(OCC)C>[CH2:27]([O:26][C:24](=[O:25])[CH2:23][C:9]([C:10]#[N:11])([C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:28]Participants
6
Conditions
- Temperature
- 20 °C
Procedure
3,4-Dichlorophenylacetonitrile (10 g, 53.75 mmol) was stirred mechanically in THF (50 mL) at -78° C. and treated dropwise with sodium bis-(trimethylsilyl)amide (108 mL, 1 M; 2 eq.). The reaction slurry was allowed to warm to 20° C. and stirred for 3 hours. The solution was cooled to -78° C. and the slurry was treated with ethyl bromoacetate (12 mL, 107 mmol, 2 eq.). The slurry was again allowed to warm to 20° C. and stirred 18 hours. The slurry was dissolved in ethyl ether and washed with water and brine. The organic phase was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel (400 g) with 20% ethyl acetate to give 15.85 g (82%) of the title compound.
Workup
- temperatureThe solution was cooled to -78° C.
- temperatureto warm to 20° C.
- stirringstirred 18 hours
- washwashed with water and brine
- dry with materialThe organic phase was dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was chromatographed on silica gel (400 g) with 20% ethyl acetate
Sources & evidence
- ORD record
- ord-8f114efb0a904159a39870f35f43475f
- Source dataset
- uspto-grants-1997_06
- Patent number
- US05635510
Reaction notes
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