Dimethyl Sulfoxide → 1-(4-Chlorophenyl)cyclobutanecarbonitrile

HRID 7813

반응식

HRID 7813 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

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. temperaturewhile maintaining the reaction temperature at 20–30° C
  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-6fd4221a2141460394cd5eff727d42ea
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087623B2

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