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Dimethylformamide → 4-Formyl-2-methoxybenzonitrile

HRID 1474236
Notes
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Reaction equation

HRID 1474236 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[O:14])=[CH:9][C:8]=1[O:15][CH3:16])(=O)=O.CCOC(C)=O.[CH3:25][N:26](C=O)C>[C-]#N.[Zn+2].[C-]#N>[CH:13]([C:10]1[CH:11]=[CH:12][C:7]([C:25]#[N:26])=[C:8]([O:15][CH3:16])[CH:9]=1)=[O:14]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 108029624-Formyl-2-methoxyphenyl trifluoromethanesulfonate

Product 1

HCID 600485344-Formyl-2-methoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Conditions

Temperature
110 °C

Procedure

A mixture of 4-formyl-2-methoxyphenyl trifluoromethanesulfonate (37.0 g, 130 mmol), zinc cyanide (61.0 g, 521 mmol) and tetrakis triphenylphosphine palladium (0) (22.6 g, 19.5 mmol) in DMF (300 mL) were stirred at 110° C. for 8 h. EtOAc was added to the reaction mixture and the organic layer was washed two times with water, dried, filtered and concentrated. The crude product was then purified by column chromatography (silica gel, ethylacetate/hexanes 3:7) which afforded 4-formyl-2-methoxybenzonitrile.

Workup

  1. washthe organic layer was washed two times with water
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was then purified by column chromatography (silica gel, ethylacetate/hexanes 3:7) which

Sources & evidence

ORD record
ord-5889e946b3534ce896afb67e1d5306c2
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09018211B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes