N-bromobutanimide → 2-(4-Methoxy-2-methylphenyl)acetonitrile

HRID 2373310

반응식

HRID 2373310 반응식
Br[N:2]1C(=O)CC[C:3]1=O.[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=1[CH3:18]>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[CH3:18][C:11]1[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:10]=1[CH2:9][C:3]#[N:2]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 784113,4-Dimethylanisole

생성물 1

HCID 38010242-(4-Methoxy-2-methylphenyl)acetonitrile수율 73.2%

시약·촉매·용매 2

HCID 6547Azobisisobutyronitrile촉매HCID 5943Carbon Tetrachloride용매

실험 절차

Under argon atmosphere, a mixture of N-bromosuccinimide (17.8 g) and 2,2′-azobisisobutyronitrile (492 mg) was added to a solution of 1,2-dimethyl-4-methoxybenzene (13.6 g) in carbon tetrachloride (200 ml). The mixture was refluxed for 6.5 hours. The reaction mixture was cooled with ice-bath. An insoluble matter was removed by filtration, and washed with carbon tetrachloride. A combined filtrate was concentrated. The residue was dissolved into N,N-dimethylformamide (100 ml) and sodium cyanide (9.86 g) was added to the mixture. The mixture was stirred over night at room temperature. The reaction mixture was poured into water, and the mixture was extracted with diethyl ether. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:n-hexane=1:6→1:4) to give the title compound (11.78 g) having the following physical data.

후처리

  1. temperatureThe mixture was refluxed for 6.5 hours
  2. temperatureThe reaction mixture was cooled with ice-bath
  3. customAn insoluble matter was removed by filtration
  4. washwashed with carbon tetrachloride
  5. concentrationA combined filtrate was concentrated
  6. dissolutionThe residue was dissolved into N,N-dimethylformamide (100 ml) and sodium cyanide (9.86 g)
  7. additionwas added to the mixture
  8. additionThe reaction mixture was poured into water
  9. extractionthe mixture was extracted with diethyl ether
  10. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated
  13. customThe residue was purified by column chromatography on silica gel (ethyl acetate:n-hexane=1:6→1:4)

출처 및 근거

ORD 기록
ord-e1bac50be7fc4e83b0633a5506251593
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07459459B2

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