Bromocyclopentane → 2-Cyclopentyloxy-3,4-dimethoxybenzonitrile

Reaction equation

[OH:1][C:2]1[C:9]([O:10][CH3:11])=[C:8]([O:12][CH3:13])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH:14]1(Br)[CH2:18][CH2:17][CH2:16][CH2:15]1>>[CH:14]1([O:1][C:2]2[C:9]([O:10][CH3:11])=[C:8]([O:12][CH3:13])[CH:7]=[CH:6][C:3]=2[C:4]#[N:5])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

Reactant 2

HCID 8728Bromocyclopentane

HCID 119947582-Hydroxy-3,4-dimethoxybenzonitrile

Product 1

HCID 184706462-Cyclopentyloxy-3,4-dimethoxybenzonitrileYield 95%

Procedure

The subtitle compound was prepared from 2-hydroxy-3,4-dimethoxybenzonitrile and freshly distilled cyclopentyl bromide following the procedure described in Example 10(d). The crude product was purified on silica gel eluting with dichloromethane to give the subtitle compound as a colourless oil (95%). Rf 0.50 (dichloromethane). MS m/z 265 MNH4)+.

Workup

customThe crude product was purified on silica gel eluting with dichloromethane

Sources & evidence

ORD record: ord-0d98e26697c64905aa4ac9f376253006
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06048864

Reaction notes

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