Dimethylformamide → HCID 21942603, compound

HRID 431871Notes

Reaction equation

HRID 431871 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:11]=[C:12](I)[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8].[CH3:15][N:16](C)C=O>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.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:15]([C:12]1[CH:11]=[C:6]([CH:5]=[C:4]([CH2:3][O:2][CH3:1])[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])#[N:16]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 21942664HCID 21942664, compound

Product 1

HCID 21942603HCID 21942603, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

After bubbling argon into a solution of methyl 3-(methoxymethyl)-5-iodobenzoate (316 mg, 1.03 mmol) in N,N-dimethylformamide (3 mL) for 5 minutes, zinc cyanide (133 mg, 1.13 mmol) and tetrakis(triphenylphosphine)palladium(0) (119 mg, 0.010 mmol) were added. The reaction mixture was heated at 80° C. for 15 minutes under argon. Following cooling, the reaction mixture was diluted with ethyl acetate and then the precipitate that formed was removed by filtration. The filtrate was washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. Silica gel chromatography using 10-30% ethyl acetate/hexanes afforded 184 mg (86%) of methyl 3-cyano-5-(methoxymethyl)benzoate as a colorless oil.

Workup

  1. temperatureFollowing cooling
  2. customthe precipitate that formed
  3. customwas removed by filtration
  4. washThe filtrate was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8ae811275e4e4bf79b2cdb03e8a0612a
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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