Process for the selective deprotonation and functionalization of 1-fluoro-2-substituted-3-chlorobenzenes

• US 7,611,647 B2
• Filed: 01/08/2009
• Issued: 11/03/2009
• Est. Priority Date: 01/11/2008
• Status: Active Grant

• Current Assignee: Corteva Agriscience LLC (Corteva, Inc.)
• Original Assignee: Dow Agrosciences LLC (Corteva, Inc.)
• Inventors: Emonds, Mark V. M., Renga, James M., Arndt, Kim E., Oppenheimer, Jossian
• Primary Examiner(s): PARSA, JAFAR F
• Application Number:
  US12/350,259
• Publication Number:
  US 20090182168A1
• Time in Patent Office: 299 Days
• Field of Search: 260/665.R, 562/473, 562/474
• US Class Current: 260/665.00R
• CPC Class Codes: C07F 1/02 Lithium compounds

Abstract

1-Fluoro-2-substituted-3-chlorobenzenes are selectively deprotonated and functionalized in the position adjacent to the fluoro substituent.

Claims

1. A process for the preparation of a lithiobeuzene of Formula I

2. The process of claim 1 in which the alkyl lithium is n-butyl lithium.

3. The process of claim 1 in which the inert organic solvent is an hydrocarbon, an ether or mixtures thereof.

4. The process of claim 1 in which X represents OR¹.

5. The process of claim 1 in which the reaction mixture is further contacted with an electrophilic reagent.

6. The process of claim 5 in which the electrophilic reagent is boronic acid esters, carbon dioxide, N,N-dialkylformamides or alkyl formates.

7. A compound of the formula