Dimethylformamide → (3-Ethyl-4-methoxyphenyl)acetonitrile

HRID 2076628Notes

Reaction equation

CN(C)C=O.Br[C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[CH2:10][C:11]#[N:12].C(=O)([O-])[O-].[K+].[K+].[CH2:24](B(CC)CC)[CH3:25]>O>[CH2:24]([C:7]1[CH:8]=[C:9]([CH2:10][C:11]#[N:12])[CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[CH3:25]

Participants

Conditions

Temperature: 70 °C

Procedure

N,N-Dimethylformamide (75 ml) was added to 3-bromo-4-methoxybenzyl cyanide (9.0 g, 40 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II)-dichloromethane adduct (400 mg, 0.49 mmol) and potassium carbonate (24.0 g, 174 mmol) at room temperature. Further, triethylborane (1M n-hexane solution, 50 ml, 50 mmol) was added dropwise thereto and the reaction mixture was stirred at 70° C. for 5 hours. After the temperature of the reaction mixture was returned to room temperature, the mixture was poured into water and extracted with ethyl acetate. The organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=8/1-5/1) to give (3-ethyl-4-methoxyphenyl)acetonitrile (2.6 g, yield: 38%) as an oil.

Workup

customwas returned to room temperature
extractionextracted with ethyl acetate
washThe organic layer was successively washed with water
dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
customThe residue obtained
customby removing the solvent under reduced pressure
customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=8/1-5/1)

Sources & evidence

ORD record: ord-be068079c85a4ba49e6ab3df1a990c1e
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07923573B2

Reaction notes

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