Dimethyl Sulfoxide → 1-(4-Chlorophenyl)cyclobutanecarbonitrile

HRID 47275

반응식

HRID 47275 반응식
CS(C)=O.[H-].[Na+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]#[N:16])=[CH:10][CH:9]=1.Br[CH2:18][CH2:19][CH2:20]Br>C(OCC)C>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2([C:15]#[N:16])[CH2:20][CH2:19][CH2:18]2)=[CH:10][CH:9]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 2415824-Chlorobenzyl cyanide

생성물 1

HCID 986211-(4-Chlorophenyl)cyclobutanecarbonitrile수율 68.2%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
25 °C

실험 절차

Into a round-bottom flask under argon fitted with an addition funnel and thermometer was added anhydrous dimethylsulfoxide and sodium hydride (1.17 g, 48.8 mmol, 95%). Then a solution of (4-chlorophenyl)acetonitrile (A) (2.70 mL, 22.2 mmol) and 1,3-dibromopropane (2.48 mL, 24.4 mmol) in diethyl ether (15 mL) was added slowly, while maintaining the reaction temperature at 20-30° C. The reaction mixture was maintained at room temperature for overnight. The reaction mixture was carefully quenched with water (50 mL) and then extracted with hexane (3×100 mL). The organic extracts were combined, washed with water (3×75 mL), brine (50 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated to give 2.9 g of 1-(4-chlorophenyl)-cyclobutanecarbonitrile, B, as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ 2.03-2.09 (m, 1H); 2.36-2.62 (m, 3H); 2.76-2.84 (m, 2H); 7.34 (s, 4H); 13C NMR (CDCl3, 75 MHz): δ 17.0, 34.6 (2C), 39.7,123.9, 127.1, 129.1, 133.7, 138.3.

후처리

  1. customInto a round-bottom flask under argon fitted with an addition funnel
  2. temperatureThe reaction mixture was maintained at room temperature for overnight
  3. customThe reaction mixture was carefully quenched with water (50 mL)
  4. extractionextracted with hexane (3×100 mL)
  5. washwashed with water (3×75 mL), brine (50 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8c8e9e85eb6d4f0f92dfdda91199c0ff
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699866B2

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