Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1164122Generated: November 4, 2026

1-Bromohexane → Ethyl 2-cyano-2-[2-methoxy-3-(o-tolylthio)phenyl]octanoate

https://huagongshe.com/reaction/1164122

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1-BromohexaneHCID 8101—
ReactantSodium hydrideHCID 24758—
ReactantEthyl 2-cyano-2-[2-methoxy-3-(o-tolylthio)phenyl]acetateHCID 20513407—
SolventDimethylformamideHCID 6228—
ProductEthyl 2-cyano-2-[2-methoxy-3-(o-tolylthio)phenyl]octanoateHCID 20513448100.3%

Reaction Steps

A solution of ethyl 2-cyano-2-[2-methoxy-3-(o-tolylthio)phenyl]acetate (4 g) in dimethylformamide (5 ml) was added dropwise to a solution of sodium hydride (purity 65%, 450 mg) in dimethylformamide (20 ml) in 10 minutes at temperature below 10° C. with stirring. After stirring the mixture at the same temperature for 10 minutes, n-hexyl bromide (3.85 g) was added to the mixture and stirred at 50° C. for an hour. After evaporation, water was added to the residue, and the mixture was extracted with diethyl ether. The extract was washed with water, dried and evaporated under reduced pressure to give oily ethyl 2-cyano-2-[2-methoxy-3-(o-tolylthio)phenyl]octanoate (5 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04367238
Source datasetuspto-grants-1983_01
ORD IDord-9c484b65327e4997b896893ba695a6f2
Source noteuspto-grants-1983_01