Hydrochloric Acid → 2-Chloro-2-(4-phenoxyphenyl)propionitrile

HRID 51215

반응식

HRID 51215 반응식
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15](C2C=CC=CC=2)=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([C:27]#[N:28])(C)C.[ClH:29]>C(Cl)Cl.[I-].[Mg+2].[I-]>[Cl:29][C:14]([C:11]1[CH:10]=[CH:9][C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:13][CH:12]=1)([CH3:15])[C:27]#[N:28]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 82115Trimethylsilyl cyanideHCID 28240562-(4-Phenoxyphenyl)-1-phenyl-1-ethanone

생성물 1

HCID 120563902-Chloro-2-(4-phenoxyphenyl)propionitrile

시약·촉매·용매 2

HCID 5462737Magnesium diiodide촉매HCID 6344Dichloromethane용매

실험 절차

A mixture of 4-phenoxyphenylacetophenone (6.36 g), trimethylsilylcyanide (3.96 g) and magnesium iodide (10 mg) in methylene chloride (30 ml) was stirred for 12 hrs at room temperature, 15% hydrochloric acid (10 ml) was then added. The mixture was again stirred for 8 hrs at room temperature. The organic layer was separated and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was dissolved in benzene (50 ml) and pyridine (2.37 g) and thionyl chloride (4.76 g) were added at 0° C. with stirring. The reaction mixture was stirred for an additional 3 hrs at room temperature and then the solvent was evaporated. The residue was purified by column chromatography to give 7.09 g of 2-chloro-2-(4-phenoxyphenyl)propionitrile as an oil.

후처리

  1. stirringThe mixture was again stirred for 8 hrs at room temperature
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. dissolutionThe residue was dissolved in benzene (50 ml)
  6. additionpyridine (2.37 g) and thionyl chloride (4.76 g) were added at 0° C.
  7. stirringwith stirring
  8. stirringThe reaction mixture was stirred for an additional 3 hrs at room temperature
  9. customthe solvent was evaporated
  10. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-ff306ddd6e434acab73221100de33b89
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713629B2

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