Synthesis of Alkyl 2-Bromomethyl-4-(diethoxyphosphorylmethyl)-5-tert-butylfuran-3-carboxylates and Their Reactions with Nucleophilic Agents

doi:10.1023/A:1025669326432

Paper

Synthesis of Alkyl 2-Bromomethyl-4-(diethoxyphosphorylmethyl)-5-tert-butylfuran-3-carboxylates and Their Reactions with Nucleophilic Agents

Published Apr 1, 2003 · L. М. Pevzner

Russian Journal of General Chemistry

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Abstract

Alkyl 2-methyl-4-(diethoxyphosphorylmethyl)-5-tert-butylfuran-3-carboxylates are selectivelybrominated with N-bromosuccinimide at the methyl group in position 2 of the ring. The resulting bromo-methyl derivatives react with secondary amines to form tertiary amines, with sodium butylthiolate inmethanol to form the corresponding sulfide. The reaction with potassium thiocyanate in DMF at 80°C givesa mixture of thiocyanate and isothiocyanate. When treated with phenolate or alcoholate ions, the bromomethylfurans decompose.

Study Snapshot

Selective bromination of alkyl 2-methyl-4-(diethoxyphosphorylmethyl)-5-tert-butylfuran-3-carboxylates with N-bromosuccinimide leads to tertiary amines, sodium butylthiolate, and sulf

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Synthesis of Alkyl 2-Bromomethyl-4-(diethoxyphosphorylmethyl)-5-tert-butylfuran-3-carboxylates and Their Reactions with Nucleophilic Agents

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References

Citations

Reaction of chloromethyl derivatives of ethyl 3-(furyl)-3-(diethoxyphosphoryl)acrylates with sodium azide and potassium thiocyanate

Chloromethyl derivatives of ethyl 3-(furyl)-3-(diethoxyphosphoryl)acrylates react with sodium azide and potassium thiocyanate to produce a mixture of thiocyanates and isothiocyanates, with some exceptions.