1,4-Dibromobutane → 1-(2-Naphthyl)cyclopentanecarbonitrile

HRID 2169255Notes

Reaction equation

HRID 2169255 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]#[N:13].Br[CH2:15][CH2:16][CH2:17][CH2:18]Br.ClC1C=CC(Cl)=CC=1C1(C#N)CCCC1>>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1([C:12]#[N:13])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 3

HCID 80561,4-DibromobutaneHCID 820082-NaphthylacetonitrileHCID 754260371-(2,5-Dichlorophenyl)cyclopentane-1-carbonitrile

Product 1

HCID 867259061-(2-Naphthyl)cyclopentanecarbonitrileYield 75.5%

Procedure

1-Naphthalen-2-yl-cyclopentanecarbonitrile (211) (25.0 g, 75.46%) was synthesized as a white solid from naphthalen-2-yl-acetonitrile (210) (25.0 g, 149.7 mmol) and 1,4-dibromobutane (17.8 mL, 149.7 mmol) following the procedure described for 1-(2,5-dichlorophenyl)-cyclopentanecarbonitrile (198).

Sources & evidence

ORD record
ord-a6df6933a2ed47829ca005d2d3237b8c
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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