1,4-Dibromobutane → 1-(Toluene-4-sulfonyl)cyclopentanecarbonitrile

HRID 2061643Notes

Reaction equation

HRID 2061643 reaction equation
[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([S:7]([CH2:10][C:11]#[N:12])(=[O:9])=[O:8])=[CH:3][CH:2]=1.Br[CH2:15][CH2:16][CH2:17][CH2:18]Br>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[C:1]1([CH3:13])[CH:2]=[CH:3][C:4]([S:7]([C:10]2([C:11]#[N:12])[CH2:18][CH2:17][CH2:16][CH2:15]2)(=[O:8])=[O:9])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 80561,4-DibromobutaneHCID 79776Tosylacetonitrile2×

Product 1

HCID 434197861-(Toluene-4-sulfonyl)cyclopentanecarbonitrileYield 84%

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Procedure

Similarly to Example 1 paragraph (a), by reaction of 2 g (10.2 mmol) of (toluene-4-sulfonyl)-acetonitrile with 1.35 ml (11.3 mmol) of 1,4-dibromobutane, 50 ml of aqueous soda solution, 233 mg (1 mmol) of benzyltriethylammonium chloride. 2.14 g of 1-(toluene-4-sulfonyl)cyclopentanecarbonitrile is obtained in the form of a brown powder. (Yield=84%)

Sources & evidence

ORD record
ord-1cf7b5ad78c34da5ba4b052e3ad64577
Source dataset
uspto-grants-2012_10
Patent number
US08283378B2

Reaction notes

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