# US 7,611,647 B2 · Process for the selective deprotonation and functionalization of 1-fluoro-2-substituted-3-chlorobenzenes

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- Number: US 7,611,647 B2
- Document ID: US7611647B2
- Status: Granted
- Kind: B2
- Application number: 12/350,259
- Filed: 2009-01-08
- Published: 2009-07-16
- Granted: 2009-11-03
- Earliest claimed: 2008-01-11
- Assignees: Dow AgroSciences LLC
- Inventors: Kim E. Arndt; Mark V. M. Emonds; James M. Renga; Jossian Oppenheimer
- Web page: https://patentgrep.com/patent/US7611647B2

## CPC

- C07F 1/02: Lithium compounds
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

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

## Claims

### Claim 1

A process for the preparation of a lithiobeuzene of Formula I
wherein
X represents F, OR1 or NR2R3;
Y represents H or F; and
R1, R2 and R3 independently represents a C1-C4 alkyl group;
which comprises contacting a substituted fluorobenzene of Formula II
wherein X, Y, R1, R2 and R3 are as previously defined with an alkyl lithium in an inert organic solvent.

### Claim 2 (depends on 1)

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

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 1)

The process of claim 1 in which X represents OR1.

### Claim 5 (depends on 1)

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

### Claim 6 (depends on 5)

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

### Claim 7

A compound of the formula
wherein
X represents OR1 or NR2R3;
Y represents H or F;
Z represents —CO2; and
R1, R2 and R3 independently represents a C1-C4 alkyl group.