Potassium Iodide → 2-(2-Chloro-3-formyl-phenoxy)-butyronitrile

HRID 1254971노트

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HRID 1254971 반응식
[Cl:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].CS(O[CH:22]([CH2:25][CH3:26])[C:23]#[N:24])(=O)=O.[I-].[K+]>CN1CCCC1=O.O>[Cl:1][C:2]1[C:3]([CH:4]=[O:5])=[CH:6][CH:7]=[CH:8][C:9]=1[O:10][CH:22]([CH2:25][CH3:26])[C:23]#[N:24]

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 5933762-Chloro-3-hydroxybenzaldehydeHCID 154676912-(Methanesulfonyloxy)-butyronitrile2회

생성물 1

HCID 595657782-(2-Chloro-3-formyl-phenoxy)-butyronitrile

시약·촉매·용매 2

HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매

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온도
100 °C

실험 절차

2-Chloro-3-hydroxy-benzaldehyde (1.0 g, 6.4 mmol) was dissolved in 10 ml N-methyl-pyrolidone at 20° C. The resultant yellow solution was degassed with argon. After addition of cesium carbonate (2.29 g, 7.0 mmol) the suspension was stirred for 20 minutes. 2-(methanesulfonyloxy)-butyronitrile (1.56 g, 9.6 mmol) and potassium iodide (0.05 g, 0.05 mmol) were then added and the reaction mixture was heated at 100° C. under microwave irradiation (Initiator™ Sixty, Biotage) for 3 minutes. After adding an additional portion of 2-(methanesulfonyloxy)-butyronitrile (0.52 g, 3.2 mmol) the reaction mixture was once again heated under microwave irradiation at 100° C. for 5 minutes. The reaction was monitored by TLC. On completion, the mixture was poured into water (0° C.) and extracted with ether. The organic layer was separated and washed with NaOH (1N), water and brine and dried with MgSO4. The crude material was purified on silicagel by flash chromatography (ethylacetate/cyclohexane) to give 2-(2-chloro-3-formyl-phenoxy)-butyronitrile as yellow oil; 1H-NMR (CDCl3) 1.25, t, 3H, 2.2 m, 2H, 4.81 dd, 1H, 7.4, m, 2H, 7.68 m, 1H, 10.5 s, 1H.

후처리

  1. customThe resultant yellow solution was degassed with argon
  2. temperaturewas once again heated under microwave irradiation at 100° C. for 5 minutes
  3. extractionextracted with ether
  4. customThe organic layer was separated
  5. washwashed with NaOH (1N), water and brine
  6. dry with materialdried with MgSO4
  7. customThe crude material was purified on silicagel by flash chromatography (ethylacetate/cyclohexane)

출처 및 근거

ORD 기록
ord-e9d785fe21714a79a57a897c6af0118b
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455663B2

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