METHODS FOR THE PREPARATION OF 5-CHLORO-2-((ETHOXYCARBONYL)AMINO)-3-METHYLBENZOIC ACID

1 . A method of preparing a compound of Formula (II)

wherein R 3 is CH 3 or Cl;

R 4 is C 1 -C 6 alkyl or C 3 -C 6 alkenyl, each optionally substituted with up to 3 halogen and up to 1 phenyl; and

X is Cl or Br, the method comprising:

(I) forming a mixture comprising:

A) a compound of Formula (I)

wherein R 1 is CH 3 or Cl; and

R 2 is C 1 -C 6 alkyl or C 3 -C 6 alkenyl, each optionally substituted with up to 3 halogen and up to 1 phenyl; and

B) an aqueous solvent, wherein the aqueous solvent is present in a concentration less than or equal to about 90% v/v;

(II) introducing a halogenation agent to the mixture;

(III) optionally removing the halogenation agent from the mixture;

(IV) optionally introducing a strong base to the mixture; and

(V) optionally cooling the mixture to a temperature in a range of from about 0° C. to about 5° C.

2 . The method of claim 1 , wherein R3 and X are each Cl.

3 . The method of claim 1 , wherein R 3 is CH 3 and X is Cl.

4 . The method of claim 1 , wherein R 4 is C 1 -C 2 alkyl.

5 . The method of claim 1 , wherein R 1 is CH 3 .

6 . The method of claim 1 , wherein R 2 is C 1 -C 2 alkyl.

7 . The method of claim 1 , wherein R 3 is CH 3 , X is Cl, and R 4 is ethyl.

8 . The method of claim 1 , wherein the aqueous solvent is present in a concentration less than or equal to about 85% v/v.

9 . The method of claim 1 , wherein the aqueous solvent is an aqueous solution of acetic acid.

10 . The method of claim 1 , wherein the aqueous solvent does not comprise hydrogen peroxide.

11 . The method of claim 1 , wherein the aqueous solvent comprises a recovered and/or recycled aqueous solvent.

12 . The method of claim 1 , wherein the halogenation agent is a chlorination agent or a bromination agent.

13 . The method of claim 1 , wherein the halogenation agent is selected from the group consisting of Cl 2 , Br 2 , and combinations thereof.

14 . The method of claim 1 , wherein the method step of introducing a halogenation agent to the mixture comprises introducing the halogenation agent to the mixture at a temperature in a range of from about 0° C. to about 35° C.

15 . The method of claim 1 , wherein the method step of removing the halogenation agent from the mixture comprises bubbling N2 through the mixture.

16 . The method of claim 1 , wherein the strong base is selected from sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, and combinations thereof.

17 . The method of claim 1 , wherein the method produces a solid product, and wherein the method further comprises a method step of filtering and/or washing the solid product.

18 . The method of claim 1 , wherein the method further comprises a method step of recovering and/or recycling the aqueous solvent.

19 . The method of claim 17 , wherein the method step of recovering and/or recycling the aqueous solvent recovers and/or recycles at least 50% v/v of the aqueous solvent.

20 . The method of claim 1 , wherein the method further comprises a method of step of recovering and/or recycling a mother liquid.

21 . (canceled)