Dimethylformamide → Ethyl 2-(4-cyanophenyl)acetate

HRID 1428790Notes

Reaction equation

HRID 1428790 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[CH3:14][N:15](C)C=O>[C-]#N.[Zn+2].[C-]#N.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:14]([C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1)#[N:15]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 7020609Ethyl 2-(4-bromophenyl)acetate

Product 1

HCID 279718Ethyl 2-(4-cyanophenyl)acetateYield 49%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

To a stirred solution of ethyl 2-(4-bromophenyl)acetate (2.1 g, 8.445 mmol) in anhydrous dimethylformamide were added zinc cyanide (1.5 g, 12.668 mmol) and tetrakis(triphenylphosphine) palladium (1.0 g, 0.845 mmol). The reaction mixture was refluxed for overnight then cooled to room temperature. The mixture was filtered using celite pad and the filtrate was evaporated. The residue was diluted with ethylacetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filterate was concentrated under reduced pressure to get the crude. The crude was purified by column chromatography. Ethyl 2-(4-cyanophenyl)acetate (0.8 g) was obtained as 49% yield.

Workup

  1. temperatureThe reaction mixture was refluxed for overnight
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated
  4. additionThe residue was diluted with ethylacetate
  5. washwashed with water and brine
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filterate was concentrated under reduced pressure
  9. customto get the crude
  10. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-df2ff429ad4e400da6d6f415d1d361e3
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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