Ethyl bromoacetate → Diethyl 3-cyano-3-(3,4-dichlorophenyl)pentanedioate

HRID 342681Notes

Reaction equation

HRID 342681 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH2:11][C:12]#[N:13])[CH:7]=[CH:8][C:9]=1[Cl:10].[H][H].Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>C1COCC1>[C:12]([C:11]([C:6]1[CH:7]=[CH:8][C:9]([Cl:10])=[C:4]([Cl:3])[CH:5]=1)([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])#[N:13]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 76690(3,4-Dichlorophenyl)acetonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 54083037Diethyl 3-cyano-3-(3,4-dichlorophenyl)pentanedioateYield 77.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

4.3 g of sodium hydride as a 60% dispersion in oil are added to a solution of 10 g of 3,4-dichlorophenylacetonitrile in 50 ml of THF and the mixture is stirred until the evolution of hydrogen has ceased. It is cooled to 0° C. and a solution of 18 g of ethyl bromoacetate in 50 ml of THF is added dropwise. The mixture is allowed to return to RT and stirred overnight. It is evaporated to dryness, the residue is taken up with ether and the mixture is washed with a buffer solution of pH 2 and dried over MgSO4. The residue is chromatographed on silica using a DCM/AcOEt mixture (80/20; v/v) as the eluent to give 15 g of the expected compound.

Workup

  1. customto return to RT
  2. customIt is evaporated to dryness
  3. washthe mixture is washed with a buffer solution of pH 2
  4. dry with materialdried over MgSO4
  5. customThe residue is chromatographed on silica using a DCM/AcOEt mixture (80/20; v/v) as the eluent

Sources & evidence

ORD record
ord-9c0955e7cc2c4db38c8d40ff3df40aaa
Source dataset
uspto-grants-1999_01
Patent number
US05859029

Reaction notes

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