JPH11512420A - ジフェニルエーテル化合物のニトロ化方法 - Google Patents
ジフェニルエーテル化合物のニトロ化方法Info
- Publication number
- JPH11512420A JPH11512420A JP9511733A JP51173397A JPH11512420A JP H11512420 A JPH11512420 A JP H11512420A JP 9511733 A JP9511733 A JP 9511733A JP 51173397 A JP51173397 A JP 51173397A JP H11512420 A JPH11512420 A JP H11512420A
- Authority
- JP
- Japan
- Prior art keywords
- mixture
- general formula
- solvent
- reaction
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/38—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. nitrodiphenyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.一般式: [式中、 R1は水素、又はC1−C6アルキル、C2−C6アルケニル若しくはC2−C6アル キニル(これらのいずれもハロゲンとOHとから選択される1個以上の置換基に よって任意に置換されることができる)、又はCOOH、COH、COOR4、 COR6、CONR4R5若しくはCONHSO2R4であり; R4とR5はそれぞれ独立的に水素又は、1個以上のハロゲン原子によって任意 に置換されるC1−C4アルキルであり; R6はハロゲン原子又はR4基である; R2は水素又はハロであり; R3はC1−C4アルキル、C2−C4アルケニル又はC2−C4アルキニルであり、 これらのいずれも1個以上のハロゲン原子、又はハロによって任意に置換される ことができる] で示される化合物の製造方法であって、 一般式II: [式中、R1、R2及びR3は一般式Iに関して定義した通りである] で示される化合物を硝酸又は硝酸と硫酸との混合物を含むニトロ化剤と、有機溶 媒の存在下かつ無水酢酸の存在下で反応させることを含み、無水酢酸の、一般式 Iの化合物に対するモル比が約1:1から3:1までであることを特徴とする方 法。 2.溶媒の、反応物(存在する全ての異性体を包含する)に対する重量比が 4.25:1以下である、請求項1記載の方法。 3.溶媒の、反応物(存在する全ての異性体を包含する)に対する重量比が 1:1から2.5:1までである、請求項2記載の方法。 4.反応溶媒が、例えばジクロロメタン(DCM)、エチレンジクロリド( EDC)、クロロホルム、テトラクロロエチレン(Perklone)及びジク ロロベンゾトリフルオリド(DCBTF)のようなハロゲン化溶媒;酢酸;アセ トニトリル;例えばテトラヒドロフラン(THF)又はジオキサンのようなエー テル;スルホラン;ニトロベンゼン;ニトロメタン;液体二酸化硫黄又は液体二 酸化炭素である、請求項1〜3のいずれかに記載の方法。 5.反応溶媒がPerkloneである、請求項4記載の方法。 6.ニトロ化剤が30〜45%の純粋硝酸を含有する、硝酸と硫酸との混合 物である、請求項1〜3のいずれかに記載の方法。 7.ニトロ化剤を反応混合物に約30分間から15時間までの時間にわたっ て加える、請求項6記載の方法。 8.一般式Iの化合物において、R2がクロロであり、R3がトリフルオロメ チルである、請求項1〜4のいずれかに記載の方法。 9.一般式Iの化合物が5−(2−クロロ−α,α,α−トリフルオロ−4 −トリルオキシ)−2−ニトロ安息香酸(Acifluorfen)又は5−( 2−クロロ−α,α,α−トリフルオロ−4−トリルオキシ)−N−メタンスル ホニル−2−ニトロベンズアミド(Fomesafen)である、請求項1〜5 のいずれかに記載の方法。 10.一般式Iの化合物がAcifluorfenであり、Acifluo rfenをその酸塩化物に転化させ、この酸塩化物をメタンスルホンアミドで処 理して、Fomesafenを得る工程をさらに含む、請求項1〜6のいずれか に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB9518705.0A GB9518705D0 (en) | 1995-09-13 | 1995-09-13 | Chemical process |
GB9518705.0 | 1995-09-13 | ||
PCT/GB1996/001892 WO1997010199A1 (en) | 1995-09-13 | 1996-08-06 | Process for nitrating diphenyl ether compounds |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH11512420A true JPH11512420A (ja) | 1999-10-26 |
JP3886533B2 JP3886533B2 (ja) | 2007-02-28 |
Family
ID=10780649
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP51173397A Expired - Lifetime JP3886533B2 (ja) | 1995-09-13 | 1996-08-06 | ジフェニルエーテル化合物のニトロ化方法 |
Country Status (18)
Country | Link |
---|---|
US (2) | US20030191341A1 (ja) |
EP (1) | EP0851852B1 (ja) |
JP (1) | JP3886533B2 (ja) |
KR (1) | KR100423572B1 (ja) |
CN (1) | CN1078885C (ja) |
AR (1) | AR003328A1 (ja) |
AT (1) | ATE191450T1 (ja) |
AU (1) | AU6663996A (ja) |
BR (1) | BR9610294A (ja) |
CA (1) | CA2229735C (ja) |
DE (1) | DE69607633T2 (ja) |
ES (1) | ES2145475T3 (ja) |
GB (1) | GB9518705D0 (ja) |
HU (1) | HU224865B1 (ja) |
IL (1) | IL123616A (ja) |
TW (1) | TW460447B (ja) |
WO (1) | WO1997010199A1 (ja) |
ZA (1) | ZA966931B (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003518088A (ja) * | 1999-12-22 | 2003-06-03 | シンジェンタ リミテッド | ジフェニルエーテル化合物の製造方法 |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6028219A (en) * | 1995-09-13 | 2000-02-22 | Zeneca Limited | Process for the nitration of diphenylethers |
TW426650B (en) * | 1996-11-01 | 2001-03-21 | Zeneca Ltd | Nitration process |
DE102007010161A1 (de) | 2007-03-02 | 2008-09-04 | Saltigo Gmbh | Verfahren zur Nitrierung substituierter Benzole in Gegenwart von Propionsäure |
CN101486654B (zh) * | 2009-03-04 | 2012-10-10 | 西安近代化学研究所 | 2-甲基-3-硝基苯乙酸合成方法 |
CN103787890A (zh) * | 2014-02-28 | 2014-05-14 | 江苏省激素研究所股份有限公司 | 一种三氟羧草醚的合成方法 |
CN105820054A (zh) * | 2016-04-26 | 2016-08-03 | 合肥工业大学 | 一种3-甲基-2-硝基苯甲酸甲酯的制备方法 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4031131A (en) * | 1975-09-29 | 1977-06-21 | Rohm And Haas Company | Process for preparing phenoxybenzoic acids |
US4400530A (en) * | 1980-06-27 | 1983-08-23 | Ppg Industries, Inc. | Process for preparing substituted diphenyl ethers |
US4594440A (en) * | 1981-07-27 | 1986-06-10 | Rhone:Pulenc, Inc. | Process for recovering and purifying herbicidal phenoxybenzoic acid derivatives |
US4405805A (en) * | 1981-07-27 | 1983-09-20 | Rhone-Poulenc, Inc. | Process for recovering and purifying herbicidal phenoxybenzoic acid derivatives |
US4424393A (en) * | 1981-08-24 | 1984-01-03 | Ppg Industries, Inc. | Process of preparation of substituted diphenyl ethers |
US4743703A (en) * | 1981-10-19 | 1988-05-10 | Rohm And Haas Company | Herbicidal 4-fluoroalkyl-4'-nitrodiphenyl ethers |
US4429146A (en) * | 1982-04-15 | 1984-01-31 | Gaf Corporation | Substituted diphenyl ether herbicides and process for use |
DE3480539D1 (en) * | 1984-01-03 | 1989-12-28 | Gen Electric | Nitration reactions with acid anhydride promoters |
SI0668260T1 (en) * | 1994-02-17 | 1998-10-31 | Zeneca Limited | Process for phosgenation in the presence of acetonitrile |
-
1995
- 1995-09-13 GB GBGB9518705.0A patent/GB9518705D0/en active Pending
-
1996
- 1996-08-06 HU HU9802863A patent/HU224865B1/hu not_active IP Right Cessation
- 1996-08-06 AT AT96926472T patent/ATE191450T1/de not_active IP Right Cessation
- 1996-08-06 KR KR10-1998-0701695A patent/KR100423572B1/ko not_active IP Right Cessation
- 1996-08-06 CA CA002229735A patent/CA2229735C/en not_active Expired - Lifetime
- 1996-08-06 BR BR9610294A patent/BR9610294A/pt not_active IP Right Cessation
- 1996-08-06 IL IL12361696A patent/IL123616A/en not_active IP Right Cessation
- 1996-08-06 EP EP96926472A patent/EP0851852B1/en not_active Expired - Lifetime
- 1996-08-06 AU AU66639/96A patent/AU6663996A/en not_active Abandoned
- 1996-08-06 WO PCT/GB1996/001892 patent/WO1997010199A1/en active IP Right Grant
- 1996-08-06 JP JP51173397A patent/JP3886533B2/ja not_active Expired - Lifetime
- 1996-08-06 ES ES96926472T patent/ES2145475T3/es not_active Expired - Lifetime
- 1996-08-06 CN CN96196918A patent/CN1078885C/zh not_active Expired - Lifetime
- 1996-08-06 DE DE69607633T patent/DE69607633T2/de not_active Expired - Fee Related
- 1996-08-13 TW TW085109806A patent/TW460447B/zh not_active IP Right Cessation
- 1996-08-15 ZA ZA966931A patent/ZA966931B/xx unknown
- 1996-08-22 AR ARP960104076A patent/AR003328A1/es active IP Right Grant
-
2003
- 2003-05-16 US US10/260,024 patent/US20030191341A1/en not_active Abandoned
-
2006
- 2006-10-30 US US11/554,076 patent/US20070055077A1/en not_active Abandoned
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003518088A (ja) * | 1999-12-22 | 2003-06-03 | シンジェンタ リミテッド | ジフェニルエーテル化合物の製造方法 |
Also Published As
Publication number | Publication date |
---|---|
EP0851852A1 (en) | 1998-07-08 |
GB9518705D0 (en) | 1995-11-15 |
DE69607633T2 (de) | 2000-08-31 |
KR19990044447A (ko) | 1999-06-25 |
ATE191450T1 (de) | 2000-04-15 |
HUP9802863A2 (hu) | 1999-03-29 |
WO1997010199A1 (en) | 1997-03-20 |
ES2145475T3 (es) | 2000-07-01 |
CA2229735A1 (en) | 1997-03-20 |
DE69607633D1 (de) | 2000-05-11 |
ZA966931B (en) | 1997-03-13 |
BR9610294A (pt) | 1999-03-16 |
CN1196045A (zh) | 1998-10-14 |
JP3886533B2 (ja) | 2007-02-28 |
US20030191341A1 (en) | 2003-10-09 |
AR003328A1 (es) | 1998-07-08 |
US20070055077A1 (en) | 2007-03-08 |
EP0851852B1 (en) | 2000-04-05 |
CA2229735C (en) | 2008-10-28 |
HUP9802863A3 (en) | 2000-08-28 |
HU224865B1 (en) | 2006-03-28 |
IL123616A (en) | 2001-06-14 |
CN1078885C (zh) | 2002-02-06 |
KR100423572B1 (ko) | 2004-07-19 |
TW460447B (en) | 2001-10-21 |
AU6663996A (en) | 1997-04-01 |
IL123616A0 (en) | 1998-10-30 |
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