4-Bromobutyronitrile → HCID 13051981, compound

HRID 1995468Notes

Reaction equation

HRID 1995468 reaction equation
[H-].[Na+].[C:3]1([CH:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H][H].Br[CH2:23][CH2:24][CH2:25][C:26]#[N:27]>CN(C)C=O>[C:26]([CH2:25][CH2:24][CH2:23][C:9]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:15]([O:17][CH2:18][CH3:19])=[O:16])#[N:27]

Participants

6

Reactant 4

HCID 214124-BromobutyronitrileHCID 24758Sodium hydrideHCID 66514Diethyl phenylmalonateHCID 178418361HCID 178418361, compound

Product 1

HCID 13051981HCID 13051981, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A 50% mineral oil dispersion containing 16.8 g (0.7 mol) of sodium hydride was placed in a 3-liter, three-necked, round-bottom flask and washed free of oil with 500 ml of dry hexane. To this was added 1.2 liters of dry dimethylformamide (DMF) and 165.4 g (0.7 mol) of diethyl phenylmalonate (Aldrich Chemical Co., Milwaukee, WI). After hydrogen ceased to be evolved (3.5 hours), 104.2 g (0.7 mol) of 4-bromobutyronitrile (Aldrich Chemical Co.) was added, and the reaction heated at 65° C. overnight. The solvent was removed under reduced pressure, and the residue suspended in 1 liter of ethyl acetate. It was filtered, the filtrate reevaporated, and the residue evaporatively distilled at 170° C./0.1 mm to give 168 g (79% yield) of the diester (15) as a yellow liquid.

Workup

  1. washthree-necked, round-bottom flask and washed free of oil with 500 ml of dry hexane
  2. additionwas added
  3. customThe solvent was removed under reduced pressure
  4. filtrationIt was filtered
  5. customthe filtrate reevaporated
  6. distillationthe residue evaporatively distilled at 170° C./0.1 mm

Sources & evidence

ORD record
ord-79f6846780ca4a048599da9472bf813f
Source dataset
uspto-grants-1983_09
Patent number
US04404366

Reaction notes

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