Dimethylformamide → HCID 70815998, compound

HRID 1843037Notes

Reaction equation

HRID 1843037 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1I.[CH3:16][N:17](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:16]([C:7]1[CH:6]=[CH:5][C:4]([CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:3][C:2]=1[F:1])#[N:17]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 70816135HCID 70816135, compound

Product 1

HCID 70815998HCID 70815998, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

To a solution of ethyl 2-(3-fluoro-4-iodophenyl)propanoate (1.15 g, 3.570 mmol) in DMF was added Zn(CN)2 (629 mg, 5.355 mmol) and Pd(PPh3)4 (825 mg, 0.714 mmol). The reaction mixture was refluxed for 8 hours and then cooled to room temperature. The mixture was filtered through a plug of Celite and concentrated. The residue was diluted with EtOAc and washed with 10% HCl solution. The organic layer was dried over MgSO4 and concentrated. The residue was purified by column chromatography to afford the pure compound ethyl 2-(4-cyano-3-fluorophenyl)propanoate (520 mg, 66%).

Workup

  1. temperatureThe reaction mixture was refluxed for 8 hours
  2. filtrationThe mixture was filtered through a plug of Celite
  3. concentrationconcentrated
  4. additionThe residue was diluted with EtOAc
  5. washwashed with 10% HCl solution
  6. dry with materialThe organic layer was dried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-404669c1fd5d4d7fa4e10161f7bbb7d0
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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