Nitrogen → Methyl 2-(4-cyano-3-fluorophenyl)propanoate

HRID 1428781Notes

Reaction equation

HRID 1428781 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]([CH3:14])[C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:6][C:7]=1I.N#N.[CH3:17][N:18](C)C=O>[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-]#N.[Zn+2].[C-]#N>[C:17]([C:7]1[CH:6]=[CH:5][C:4]([CH:9]([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:3][C:2]=1[F:1])#[N:18]

Participants

6

Reactant 3

HCID 947NitrogenHCID 6228DimethylformamideHCID 70855905Methyl 2-(3-fluoro-4-iodophenyl)propanoate

Product 1

HCID 58915206Methyl 2-(4-cyano-3-fluorophenyl)propanoate

Reagents, catalysts & solvents 2

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

Conditions

Temperature
120 °C

Procedure

Methyl 2-(3-fluoro-4-iodophenyl)propanoate, tetrakis(triphenylphosphine) palladium(0) and zinc cyanide are placed in dimethylformamide and charged with N2. The reaction mixture was stirred at 120° C. for 15 h and cooled to room temperature. The reaction mixture is filtered by celite packed filter, washed with ethyl acetate. After concentrate solvent, residue is purified on a silica gel column using ethylacetate-hexane as solvent system to give methyl 2-(4-cyano-3-fluorophenyl)propanoate.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe reaction mixture is filtered by celite
  3. filtrationpacked filter
  4. washwashed with ethyl acetate
  5. concentrationAfter concentrate solvent, residue
  6. customis purified on a silica gel column

Sources & evidence

ORD record
ord-a740748b80e3458b804da76265de57a5
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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