JP2526937B2 - 4-acetylamino-3-fluorophenol - Google Patents
4-acetylamino-3-fluorophenolInfo
- Publication number
- JP2526937B2 JP2526937B2 JP62284810A JP28481087A JP2526937B2 JP 2526937 B2 JP2526937 B2 JP 2526937B2 JP 62284810 A JP62284810 A JP 62284810A JP 28481087 A JP28481087 A JP 28481087A JP 2526937 B2 JP2526937 B2 JP 2526937B2
- Authority
- JP
- Japan
- Prior art keywords
- fluorophenol
- acetylamino
- present
- compound
- reaction
- 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.)
- Expired - Lifetime
Links
Description
【発明の詳細な説明】 本発明は新規なフェノール誘導体に関するものであ
る。さらに詳しくは、特開昭61−76486号公報に記載の
除草剤等を製造する上で有用な製造原料である４−アセ
チルアミノ−３−フルオロフェノール（以下、本発明化
合物と記す）を提供するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel phenol derivative. More specifically, 4-acetylamino-3-fluorophenol (hereinafter referred to as the compound of the present invention), which is a raw material useful for producing the herbicides described in JP-A-61-76486, is provided. It is a thing.
まず、本発明化合物の製造法について説明する。 First, the method for producing the compound of the present invention will be described.
本発明化合物は、J.Chem.Soc.1964年473頁に記載の方
法等により得られる４−アミノ−３−フルオロフェノー
ルと塩化アセチル無水酢酸等のアセチル化剤とを必要に
より塩基の存在下に反応させることによって製造され
る。The compound of the present invention contains 4-amino-3-fluorophenol obtained by the method described in J. Chem. Soc. 1964, p. 473, etc., and an acetylating agent such as acetyl chloride anhydride in the presence of a base, if necessary. It is produced by reacting.
該反応は、通常４−アミノ−３−フルオロフェノール
１当量に対してアセチル化剤は1.0〜5.0当量用いられ、
塩基は必要によりピリジン、ピコリン、トリエチルアミ
ン、N,N−ジエチルアニリン、４−（N,N−ジメチルアミ
ノ）ピリジン等の有機塩基が５当量程度まで用いられ
る。In the reaction, the acetylating agent is usually used in an amount of 1.0 to 5.0 equivalents to 1 equivalent of 4-amino-3-fluorophenol,
As the base, if necessary, an organic base such as pyridine, picoline, triethylamine, N, N-diethylaniline, 4- (N, N-dimethylamino) pyridine or the like is used up to about 5 equivalents.
用いられる反応溶媒としては、例えば、ヘキサン、ヘ
プタン、リグロイン等の脂肪族炭化水素類、ベンゼン、
トルエン、キシレン等の芳香族炭化水素類、ジクロロメ
タン、クロロホルム、四塩化炭素、1,2−ジクロロエタ
ン、1,1,1−トリクロロエタン、クロロベンゼン、ジク
ロロベンゼン等のハロゲン化炭化水素類、ジイソプロピ
ルエーテル、ジオキサン、エチレングリコールジメチル
エーテル、ジエチレングリコールジメチルエーテル、ト
リエチレングリコールジメチルエーテル、テトラヒドロ
フラン等のエーテル類、酢酸、N,N−ジメチルホルムア
ミド、N,N−ジメチルアセトアミド、ジメチルスルホキ
シド、スルホラン等あるいはそれらの混合物があげられ
る。The reaction solvent used, for example, hexane, heptane, aliphatic hydrocarbons such as ligroin, benzene,
Toluene, aromatic hydrocarbons such as xylene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane, chlorobenzene, halogenated hydrocarbons such as dichlorobenzene, diisopropyl ether, dioxane, Examples thereof include ethers such as ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, and tetrahydrofuran, acetic acid, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, sulfolane, and the like, or a mixture thereof.
反応温度は通常20〜200℃、好ましくは50〜90℃であ
る。The reaction temperature is generally 20 to 200 ° C, preferably 50 to 90 ° C.
反応終了後は、有機溶媒抽出および濃縮等の通常の後
処理を行い、必要により再結晶、クロマトグラフィー等
の操作を行う。After completion of the reaction, usual post-treatments such as extraction with an organic solvent and concentration are carried out, and if necessary, operations such as recrystallization and chromatography are carried out.
本発明化合物は下記の経路により、有用な除草性化合
物である２−〔４−置換−７−フルオロ−2H−1,4−ベ
ンゾオキサジン−３（4H）−オン−６−イル〕−4,5,6,
7−テトラヒドロ−2H−イソインドール−1,3−ジオンに
導かれる。The compound of the present invention is a useful herbicidal compound, 2- [4-substituted-7-fluoro-2H-1,4-benzoxazin-3 (4H) -on-6-yl] -4, by the following route. 5,6,
Directed to 7-tetrahydro-2H-isoindole-1,3-dione.
〔式中、Ｒはアルキル基、アルケニル基、アルキニル基
またはアルコキシアルキル基を表わし、Ｒ′はアルキル
基を表わす。〕 以下、本発明化合物の製造例を具体例にて示すが本発
明は下記の例のみに限定されるものではない。 [In the formula, R represents an alkyl group, an alkenyl group, an alkynyl group or an alkoxyalkyl group, and R'represents an alkyl group. Hereinafter, production examples of the compound of the present invention will be shown in specific examples, but the present invention is not limited to the following examples.
製造例 ４−アミノ−３−フルオロフェノール10.1gを酢酸81.
49gに溶かし、無水酢酸8.92gを加え75℃で２時間加熱攪
拌した。反応液を放冷後氷水にあけ、酢酸エチルで抽出
し、水洗後乾燥、次いで減圧下に溶媒を留去して、残渣
をシリカゲルクロマトグラフィー（展開溶媒；酢酸エチ
ル：ヘキサン＝1:1）に付し、４−アセチルアミノ−３
−フルオロフェノール6.3gを得た。Production Example 4-amino-3-fluorophenol 10.1 g acetic acid 81.
It was dissolved in 49 g, 8.92 g of acetic anhydride was added, and the mixture was heated with stirring at 75 ° C. for 2 hours. The reaction solution is allowed to cool, then poured into ice water, extracted with ethyl acetate, washed with water, dried, and then the solvent is distilled off under reduced pressure, and the residue is subjected to silica gel chromatography (developing solvent; ethyl acetate: hexane = 1: 1). Attached, 4-acetylamino-3
-6.3 g of fluorophenol are obtained.
mp 114〜115℃mp 114-115 ° C
Claims (1)
ール。1. Acetylamino-3-fluorophenol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62284810A JP2526937B2 (en) | 1987-11-10 | 1987-11-10 | 4-acetylamino-3-fluorophenol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62284810A JP2526937B2 (en) | 1987-11-10 | 1987-11-10 | 4-acetylamino-3-fluorophenol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01125355A JPH01125355A (en) | 1989-05-17 |
| JP2526937B2 true JP2526937B2 (en) | 1996-08-21 |
Family
ID=17683305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62284810A Expired - Lifetime JP2526937B2 (en) | 1987-11-10 | 1987-11-10 | 4-acetylamino-3-fluorophenol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2526937B2 (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6036449A (en) * | 1983-08-09 | 1985-02-25 | Sumitomo Chem Co Ltd | Preparation of phenol derivative |
-
1987
- 1987-11-10 JP JP62284810A patent/JP2526937B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH01125355A (en) | 1989-05-17 |
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