Isopropanol → 1-(4-Chlorophenyl)cyclobutanecarbonitrile

HRID 720022Notes

Reaction equation

HRID 720022 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.Br[CH2:12][CH2:13][CH2:14]Br.[H-].[Na+].CC(O)C>CCOCC.CS(C)=O.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2([C:7]#[N:8])[CH2:14][CH2:13][CH2:12]2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 3776IsopropanolHCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 2415824-Chlorobenzyl cyanide

Product 1

HCID 986211-(4-Chlorophenyl)cyclobutanecarbonitrileYield 70%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 3.37 g (22.2 mmol) of 4-Chlorobenzyl cyanide and 4.93 g (24.4 mmol) of 1,3-dibromopropane in 15 mL of ether was added dropwise into 1.17 g (48.8 mmol) of NaH in 60 mL of DMSO. The temperature was held between 25° and 35° by water bath cooling. The mixture was stirred at room temperature for 18 hours. The mixture was cooled in ice water and 3 mL of 2-propanol was added dropwise, followed by the addition of 50 mL of water. The mixture was extracted with hexane (3×100 mL), and the combined extracts were washed with water (3×75 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated to yield 2.9 g (70%) product as colorless oil. 1H NMR (CDCl3) δ 2.04–2.15 (m, 1H), 2.39–2.52 (m, 1H), 2.55–2.65 (m, 2H), 2.79–2.88 (m, 2H), 7.38 (s, 4H). 13C NMR (CDCl3) 17.3, 34.9, 40.0, 124.2, 127.3, 129.4, 134.1, 138.6.

Workup

  1. customThe temperature was held between 25° and 35° by water bath
  2. temperaturecooling
  3. extractionThe mixture was extracted with hexane (3×100 mL)
  4. washthe combined extracts were washed with water (3×75 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-825850ef2bf84498963ec4d05902ebf4
Source dataset
uspto-grants-2006_11
Patent number
US07132551B2

Reaction notes

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