Claims
- 1. A process for the preparation of a compound of general formula I: ##STR13## wherein: R.sup.1 is hydrogen or C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl or C.sub.2 -C.sub.6 alkynyl, any of which may optionally be substituted with one or more substituents selected from halogen and OH; or COOR.sup.4, COR.sup.6, CONR.sup.4 R.sup.5 or CONHSO.sub.2 R.sup.4 ;
- R.sup.4 and R.sup.5 are each independently hydrogen or C.sub.1 -C.sub.4 alkyl optionally substituted with one or more halogen atoms;
- R.sup.6 is a halogen atom or a group R.sup.4 ;
- R.sup.2 is hydrogen or halo;
- R.sup.3 is C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl or C.sub.2 -C.sub.4 alkynyl, any of which may optionally be substituted with one or more halogen atoms; or halo;
- the process comprising reacting a compound of general formula II: ##STR14## wherein R.sup.1, R.sup.2 and R.sup.3 are as defined for general formula I; with a nitrating agent comprising a mixture of nitric and sulphuric acids in the presence of an organic solvent and in the presence of acetic anhydride, wherein the molar ratio of acetic anhydride to compound of general formula II is from about 1:1 to 3:1 and the organic solvent is tetrachloroethylene (perklone) and wherein the sulphuric and nitric acids are added sequentially to the reaction mixture.
- 2. A process as claimed in claim 1, wherein the weight ratio of solvent to compound of formula II (including any isomers present) is no greater than 4.25:1.
- 3. A process as claimed in claim 2, wherein the weight ratio of solvent to compound of formula II (including any isomers present) is from 1:1 to 2.5:1.
- 4. A process as claimed in claim 1, wherein the nitrating agent is added to the reaction mixture over a period of about 30 minutes to 15 hours.
- 5. A process according to claim 1, wherein the ratio of sulphuric acid:compound of formula II is from 0.1:1 to 0.3:1.
- 6. A process as claimed in claim 1, wherein the reaction is performed at a temperature of from about -15.degree. C. to 15.degree. C.
- 7. A process as claimed in claim 6, wherein the reaction is performed at a temperature of from -10.degree. C. to 10.degree. C.
- 8. A process as claimed in claim 1, wherein, in the compound of general formula I, R.sup.2 is chloro and R.sup.3 is trifluoromethyl.
- 9. A process as claimed in claim 1, wherein the compound of general formula I is 5-(2-chloro-.alpha.,.alpha.,.alpha.-trifluoro-4-tolyloxy)-2-nitrobenzoic acid (acifluorfen) or 5-(2-chloro-.alpha.,.alpha.,.alpha.-trifluoro-4-tolyloxy)-N-methanesulphonyl-2-nitrobenzamide (fomesafen).
- 10. A process as claimed in claim 1, wherein the compound of general formula I is acifluorfen and which further comprises the steps of converting the acifluorfen to its acid chloride and treating the acid chloride with methane sulphonamide to give fomesafen.
- 11. A process as claimed in claim 1, wherein the nitrating agent is a mixture of nitric and sulphuric acids containing from 30 to 45% of pure nitric acid.
- 12. A process as claimed in claim 1 wherein the nitric acid is greater than 90% strength.
Priority Claims (1)
Number |
Date |
Country |
Kind |
9518705 |
Sep 1995 |
GBX |
|
Parent Case Info
This application is a continuation-in-part of U.S. patent application Ser. No. 08/712,695, filed on Sep. 11, 1996.
US Referenced Citations (6)
Foreign Referenced Citations (16)
Number |
Date |
Country |
003416 |
Aug 1979 |
EPX |
022610 |
Jan 1981 |
EPX |
114299 |
Aug 1984 |
EPX |
147798 |
Jul 1985 |
EPX |
274194 |
Jul 1988 |
EPX |
668260 |
Aug 1995 |
EPX |
332 28 17 |
Jun 1985 |
DEX |
1419209 |
Dec 1975 |
GBX |
1478428 |
Jun 1977 |
GBX |
2103214A |
Feb 1983 |
GBX |
2152817 |
Aug 1985 |
GBX |
2154235 |
Sep 1985 |
GBX |
2205749 |
Dec 1988 |
GBX |
9419310 |
Sep 1994 |
WOX |
9419310 |
Sep 1994 |
WOX |
WO 9819978 |
May 1998 |
WOX |
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
712695 |
Sep 1996 |
|