Potassium Carbonate → Methyl 3-t-butyl-5-cyano-4-methoxybenzoate

HRID 385032Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13](I)[C:14]=1[O:15][CH3:16])[C:8]([O:10][CH3:11])=[O:9])([CH3:4])([CH3:3])[CH3:2].[Cu](C#N)[C:19]#[N:20].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([C:19]#[N:20])[C:14]=1[O:15][CH3:16])[C:8]([O:10][CH3:11])=[O:9])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 150 °C

Procedure

Methyl 3-t-butyl-5-iodo-4-methoxybenzoate (2.77 g) was dissolved in N,N-dimethylformamide (30 mL), and copper cyanide (965 mg) was added to the solution, and then the mixture was stirred at 150° C. for 2.5 hours. To the reaction solution, 10% potassium carbonate was added, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1) to obtain the title compound (1.48 g) as a yellow oily substance.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with water and saturated brine
dry with materialdried over anhydrous sodium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record: ord-79bf890520de4991aac52a1975466a47
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367843B2

Reaction notes

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