Dimethylformamide → 4-Formyl-2-methoxybenzonitrile
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]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- washthe organic layer was washed two times with water
- customdried
- filtrationfiltered
- concentrationconcentrated
- customThe crude product was then purified by column chromatography (silica gel, ethylacetate/hexanes 3:7) which
Sources & evidence
- ORD record
- ord-027cf47f1fc44dc88b16f73748747088
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08673920B2
Reaction notes
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