AN IMPROVED ONE POT, ONE STEP PROCESS FOR THE HALOGENATION OF AROMATICS USING SOLID ACID CATALYSTS

Title:

AN IMPROVED ONE POT, ONE STEP PROCESS FOR THE HALOGENATION OF AROMATICS USING SOLID ACID CATALYSTS

Document Type and Number:

WIPO Patent Application WO/2017/163262

Kind Code:

A4

Abstract:

The present invention disclosed an improved one pot, one step process for halogenation of compound of formula (II) to afford corresponding halogenated compound of formula (I) having improved yield and increased selectivity under very mild conditions.

Inventors:

UMBARKAR SHUBHANGI BHALCHANDRA (IN)
KULAL ATUL BALASAHEB (IN)
DESHMUKH AMAR JAYWANT (IN)

Application Number:

PCT/IN2017/050097

Publication Date:

November 09, 2017

Filing Date:

March 17, 2017

Export Citation:

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Assignee:

COUNCIL SCIENT IND RES (IN)

International Classes:

C07C17/12; C07C25/02

Attorney, Agent or Firm:

REMFRY & SAGAR (IN)

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Claims:

AMENDED CLAIMS

received by the International Bureau on 18 September 2017 (18.09.2017)

CLAIMS:

1. An improved one pot, one step process for the halogenation of substituted aromatic compound comprises addition of halogenating agent and solid acid catalyst to the mixture of substituted aromatic compound in solvent followed by stirring the reaction mixture at temperature in the range of 25 to 85°C for the period in the range of 2 to 6 hrs to afford corresponding halogenated compound wherein said solid acid catalyst is selected from Si0₂, Mo0₃/Ti0₂, Mo0₃/Ti0₂, W0₃/Ti0₂, W0₃/Ti0₂and Mo Si/Al (7.5).

2. The process as claimed in claim 1, wherein said substituted aromatic compound is selected from aminoaromatic compound, hydroxy aromatic compound, aromatic aldehyde compound, halo substituted aromatics, amide substituted aromatic compound.

3. The process as claimed in claim 2, wherein said aminoaromatic compound is selected from aniline, 4-Chloroaniline, 4- Bromoaniline, 2,6 dimethyl aniline, anthranilamide, 2,6 diethyl aniline.

4. The process as claimed in claim 2, wherein said hydroxy aromatic compound is selected from phenol.

5. The process as claimed in claim 2, wherein said aromatic aldehyde compound benzaldehyde.

6. The process as claimed in claim 1, wherein said corresponding halogenated compound is selected from 4-chloro-2-iodoaniline, 2-iodoaniline, 4-bromo-2- iodoaniline, 4-iodo-2,6-dimethylaniline, 3-iodobenzaldehyde, 2-iodophenol, 2- amino-3-iodobenzamide, 2,6-diethyl-4-iodoaniline, 4-chloro-2,6-dimethylaniline and 4-bromo-2,6-dimethylaniline.

7. The process as claimed in claim 1, wherein said solvent is selected from ethylene dichloride, methanol, hexane, toluene, dichloromethane, ethanol, higher alcohols, dimethylsulfoxide, dioxane, dimethylformamide, acetone, diethyl ether, butanol and benzylalcohol.

8. The process as claimed in claim 1, wherein selectivity towards corresponding ortAo-halogenated compound is in the range of 50 to 100%.

9. The process as claimed in claim 1, wherein said process is carried out in batch mode or continuous mode.

10. The process as claimed in claim 1, wherein said halogenating agent is selected from chlorine, bromine or iodine.

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