Potassium Iodide → 2-(2-Methyl-3-trifluoromethyl-phenoxy)-butyronitrile

HRID 455322노트

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HRID 455322 반응식
CS([O:5][CH:6]([CH2:9][CH3:10])[C:7]#[N:8])(=O)=O.[CH3:11][C:12]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:15]=[CH:14][C:13]=1O.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C.O.C(OC)(C)(C)C>[CH3:11][C:12]1[C:17]([C:18]([F:19])([F:20])[F:21])=[CH:16][CH:15]=[CH:14][C:13]=1[O:5][CH:6]([CH2:9][CH3:10])[C:7]#[N:8]

참가 물질

8

반응물 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 154676912-(Methanesulfonyloxy)-butyronitrileHCID 201116982-Methyl-3-(trifluoromethyl)phenol

생성물 1

HCID 670178622-(2-Methyl-3-trifluoromethyl-phenoxy)-butyronitrile

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 15413tert-Butyl methyl ether용매

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온도
80 °C

실험 절차

A mixture of 2-(methanesulfonyloxy)-butyronitrile (449 mg, 2.75 mmol), 2-methyl-3-trifluoromethylphenol (440 mg, 2.5 mmol), potassium carbonate (432 mg, 3.13 mmol) and potassium iodide (42 mg, 0.25 mmol) in acetonitrile (20 ml) was stirred overnight at 80° C. The mixture was shaken between tBuOMe and water, washed with NaCl (aq. satd) and the ethereal phase dried with MgSO4 and evaporated. The crude product was chromatographed on silica with EtOAc and hexane to give 2-(2-methyl-3-trifluoromethyl-phenoxy)-butyronitrile. 1H-NMR (CDCl3) 1.20 t, 3H; 2.15 dt, 2H; 2.36 s, 3H; 4.75, t, 2H; 7.17, d, 1H; 7.28, t, 1H; 7.37 d, 1H.

후처리

  1. washwashed with NaCl (aq. satd)
  2. dry with materialthe ethereal phase dried with MgSO4
  3. customevaporated
  4. customThe crude product was chromatographed on silica with EtOAc and hexane

출처 및 근거

ORD 기록
ord-dbdf93172c13420ebc420505bb91342d
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497293B2

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