Dimethyl Sulfoxide → 1-(4-Chlorophenyl)cyclobutanecarbonitrile

HRID 47275

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-8c8e9e85eb6d4f0f92dfdda91199c0ff
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06699866B2

Linked notes

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