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

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

wherein

X represents F, OR 1 or NR 2 R 3 ;

Y represents H or F; and

R 1 , R 2 and R 3 independently represents a C 1 -C 4 alkyl group;

which comprises contacting a substituted fluorobenzene of Formula II

wherein X, Y, R 1 , R 2 and R 3 are as previously defined with an alkyl lithium in an inert organic solvent.

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 OR 1 .

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

wherein

X represents OR 1 or NR 2 R 3 ;

Y represents H or F;

Z represents —CO 2 ; and

R 1 , R 2 and R 3 independently represents a C 1 -C 4 alkyl group.