Industrial Consultancy & Sponsored Research (IC&SR) , IIT Madras

A One Step Synthesis of 2-substituted Benzo[b]thiophenes

Technology Category/Market

Technology: One step synthesis of 2-substituted benzo[b]thiophene;

Industry: Catalyst Manufacturing.

Applications: Manufacturing chemical.

Market: The global catalyst market is projected to grow at a CAGR of 4.6% during forecast period of 2023 to 2030.

Image

Problem Statement

  • Synthesis of 2-substituted benzo[b]thiophene derivatives were earlier from the acylation of benzo[b]thiophene using acyl source like acetyl chloride, acetic anhydride, 2-oxocarboxylic acid, N, N-dimethylacetamide, acetaldehyde and benzoyl chloride.
  • These reactions yielded major amount of 3-substituted & minor amount of 2-substituted benzo[b]thiophenes due to the high reactivity of C-3 than C-2 position of benzo[b]thiophene.
  • Expensive starting materials, handling of butyl lithium, high temperature, inert atmosphere, synthesized beta zeolite to utilize for the industrial scale preparation of 2-substituted benzo[b]thiophene will be very difficult.
  • Further a few Non-patent literatures discussed regarding the developing of the catalyst using synthesis with other associated issues.
  • Present invention has addressed said issues efficiently.

Technology

  • Present invention describes one step synthesis of 2-substituted benzo[b]thiophene.
  • The General formula includes

The process explains in smart chart herein:

  • The synthesis of 2-substituted benzo[b]thiophenes is by reacting the starting materials substituted or unsubstituted 2-halogenobenzaldehyd;
  • substituted or unsubstituted acetyl/phenacyl bromide with a catalyst, a sulphur source and phase transfer catalyst in an aqueous medium;
  • Said aqueous medium with atmospheric air and at temperature in the range of 25°C- 30°C.

Key Features/Value Proposition

Technical Perspective:

  • Present Patent facilitates the  syntheses of 2-acylbenzo[b]thiophene in a one-step direct synthesis from commercially available starting materials & cost-effective.
  • The starting material is one of 2-iodobenzaldehyde, 2-iodo-5-methylbenzaldehyde, 5-bromo-2-iodobenzaldehyde, 2-iodobenzophenone, 2-iodochalcones, 2-iodobenzaldehyde, & further the starting material is one of phenacyl bromide, acetyl bromide, 2-bromocycloalkanone, 2-bromotetralone and 2- bromoindanone.
  • The catalyst used in the subject invention is copper acetate including Sulphur source as potassium ethyl Xanthate.
  • There is no toxic solvent used in the present invention, hence the process is eco-friendly.

Industrial Perspective:

  • Patented process is environmental-friendly as it uses water as a solvent.
  • Said process is energy efficient as the reaction is performed at ambient room temperature a range of (25°C-30°C).
  • The yield of 2-acylbenzo[b]thiophene obtained by said process is higher (the yield is 95%).
Questions about this Technology?

Contact for Licensing

Research Lab

Prof. Govindasamy Sekar

Department of Chemistry

 

Intellectual Property

  • IITM IDF Ref. 1879

  • Patent No.384111;

  • PCT Application No. PCT/IN2020/050716

Technology Readiness Level

TRL- 4

Proof of Concept & validated in Lab

error: Content is protected !!