Dimethylformamide → [2-Chloro-5-(methoxymethoxy)phenyl]acetonitrile

HRID 420550노트

반응식

HRID 420550 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9]COC)=[CH:4][C:3]=1[CH3:13].Br[N:15]1C(=O)CC[C:16]1=O.[C-]#N.[Na+].CN(C)[CH:27]=[O:28]>C(Cl)(Cl)(Cl)Cl.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][O:28][CH3:27])=[CH:4][C:3]=1[CH2:13][C:16]#[N:15]

참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 67184N-bromobutanimideHCID 22467254HCID 22467254, 화합물

생성물 1

HCID 57966326[2-Chloro-5-(methoxymethoxy)phenyl]acetonitrile

시약·촉매·용매 3

HCID 962Water용매HCID 5943Carbon Tetrachloride용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 2-chloro-5-(methoxyethoxy)toluene (5.00 g; 26.8 mmol), N-bromosuccinimide (4.77 g; 26.8 mmol) and 2,2-azobis(isobutyronitrile) (0.09 g; 0.53 mmol) in carbon tetrachloride (25 ml) was refluxed for 2 hours. After air cooling and filtration the precipitate, the filtrate was condensed under reduced pressure. To the residue were added sodium cyanide (2.77 g; 80.4 mol) and anhydrous N,N-dimethylformamide (30 ml). The mixture was stirred at room temperature for 2 hours. Water and ethyl acetate were added to the reaction solution and extracted. The organic layer was washed with brine, dried over anhydrous sodium sulphate, and evaporated under reduced pressure. The residue was purified by column chromatograph on silica gel (hexane:ethyl acetate=6:1→4:1) to give [2-chloro-5-(methoxymethoxy)phenyl]acetonitrile as colorless oil (2.64 g; 47%).

후처리

  1. temperaturewas refluxed for 2 hours
  2. temperatureAfter air cooling
  3. filtrationfiltration the precipitate
  4. customcondensed under reduced pressure
  5. extractionextracted
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulphate
  8. customevaporated under reduced pressure
  9. customThe residue was purified by column chromatograph on silica gel (hexane:ethyl acetate=6:1→4:1)

출처 및 근거

ORD 기록
ord-eccd55db5c514dd491397726262db87f
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08097610B2

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