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

HRID 455322ノート

反応式

HRID 455322 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 15413tert-Butyl methyl ether溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-dbdf93172c13420ebc420505bb91342d
出典データセット
uspto-grants-2013_07
特許番号
US08497293B2

反応ノート

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