JPS5818360A - Preparation of 2-bromo-6-phenoxypyridine - Google Patents
Preparation of 2-bromo-6-phenoxypyridineInfo
- Publication number
- JPS5818360A JPS5818360A JP56116658A JP11665881A JPS5818360A JP S5818360 A JPS5818360 A JP S5818360A JP 56116658 A JP56116658 A JP 56116658A JP 11665881 A JP11665881 A JP 11665881A JP S5818360 A JPS5818360 A JP S5818360A
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen bromide
- phenoxypyridine
- bromo
- raw material
- chloro
- 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.)
- Pending
Links
Landscapes
- Pyridine Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は２−クロル−６−フェノキシビリジンを臭化水
素と反応させるととｔｌ−特徴とする２−ブロムー６−
フェノキシビリジンｔ−ｍａする方法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention provides that when 2-chloro-6-phenoxyviridine is reacted with hydrogen bromide, tl-characterized 2-bromo-6-
The present invention relates to a method for treating phenoxyviridine t-ma.
日本公開特許公報特願昭５６−５２２４には。In Japanese Patent Application Publication No. 56-5224.
２−ハロゲノ−６−フェノキシビリジン〔■〕カラ殺虫
剤等の原料として有用な６−フニノキシビコリンアルデ
ヒド叩を有利にｉ造する方法が記されている。2-Halogeno-6-phenoxypyridine [■] A method for advantageously producing 6-phynoxybicolinaldehyde, which is useful as a raw material for insecticides and the like, is described.
式（１）
〔式中、Ｘはハロゲン原子を示す。〕
一般に、ハロゲン化アリールと金属マグネシウムを反応
させる場合、ハロゲン原子の違いにより９反応性の異な
る場合が多い。（シェリー・マーチ、アドバンスト・オ
ーガニック・ケミストリー。Formula (1) [wherein, X represents a halogen atom]. ] Generally, when reacting an aryl halide with magnesium metal, the reactivity often differs depending on the difference in halogen atoms. (Sherry March, Advanced Organic Chemistry.
４７５〜４７６頁、マクグロウ・ヒル・ブック・カンパ
ニー等を参照）
すなわち９反応条件によっては塩素化子り一ル化合物上
抄は臭素化子り一ル化合物が好ましい場合もある。従っ
て、一般的に入手し易い塩素化アリール化合物を臭素化
アリール化合物に変換することは工業的に有意義なこと
といえる。(See pages 475-476, McGraw-Hill Book Company, etc.) In other words, depending on the reaction conditions, brominated monolyl compounds may be preferable in place of chlorinated monolyl compounds. Therefore, it can be said that it is industrially meaningful to convert generally easily available chlorinated aryl compounds into brominated aryl compounds.
我々は、現在工業的に安価に製造できうる２−クロル−
６−フェノキシビリジンについて鋭意研究を重ねた結果
、これを臭化水素と反応させることにより容易にかつ収
率よく２−ブロム−６−フェノ中ジピリジンに変換でき
ることを見いだし本発明を完成した。We currently have 2-chlor-
As a result of intensive research on 6-phenoxypyridine, the present invention was completed by discovering that it can be easily converted into 2-bromo-6-phenodipyridine in good yield by reacting it with hydrogen bromide.
以下２反応式（２）全示して詳細に説明を加える。The following two reaction formulas (2) will be fully shown and explained in detail.
反応式（２）
反応式（２）において用いられる臭化水素は例えば臭化
水素水、臭化水素ガスともに使用する事ができるが、好
ましくは臭化水素ガスがよい。Reaction Formula (2) The hydrogen bromide used in Reaction Formula (2) can be, for example, both hydrogen bromide water and hydrogen bromide gas, but hydrogen bromide gas is preferred.
反応に用いる溶媒としては、クロルベンゼン。Chlorbenzene is used as a solvent for the reaction.
トルエンなどの置換ベンゼン類あるいは酢酸などの極性
有機溶媒がある。特に酢酸が好ましく臭化水素として臭
化水素ガスを用いる場合には無水の酢酸が特に好ましい
。These include substituted benzenes such as toluene and polar organic solvents such as acetic acid. Acetic acid is particularly preferred, and when hydrogen bromide gas is used as hydrogen bromide, acetic anhydride is particularly preferred.
反応温度は１反応に用いる溶媒の沸点附近が好ましく１
反応時間は一般的には１〜４０時間であるが、特に臭化
水素ガスを用いる場合には。The reaction temperature is preferably around the boiling point of the solvent used in reaction 1.
The reaction time is generally 1 to 40 hours, especially when hydrogen bromide gas is used.
単位時間あたりのガスの導入量を少なくして長い時間を
かけて反応させた方がよい。It is better to reduce the amount of gas introduced per unit time and allow the reaction to take a longer time.
次に実施例を示し、更に本発明の詳細を具体的に説明す
るが２本発明はこれのみに限定されない。EXAMPLES Next, the present invention will be specifically explained with reference to Examples, but the present invention is not limited thereto.
実施例 臭化水素ガスを用いた製造方法゛ ２−ク
ロ、Ｉ＋、 −１，−フェノキシピリジン１０．３２を
２００謡の無水の酢酸に溶解させ加熱還流させた。この
混合溶液をかきまぜながら公知の方法（新実験化学講座
第８巻Ａ１第１１２頁。Example Production method using hydrogen bromide gas 10.32 of 2-chloro, I+, -1,-phenoxypyridine was dissolved in 200 g of anhydrous acetic acid and heated to reflux. While stirring this mixed solution, a known method (New Experimental Chemistry Course, Volume 8, A1, Page 112).
臭素５２７り、チ）・ラリン１７８ｖを用いた）によ如
、９時間かけて少量ずつ発生させた臭化水素ガスを吹き
込んだ。この反応混合物を放冷したのち、氷水を加え更
にエチルエーテルを１００〇−加えて抽出操作を行なっ
た。有機層を炭酸水素ナトリウム水溶液で洗浄後無水の
硫酸ナトリウムで乾燥し、溶媒を留去して白色結晶とし
て粗生成物を得た。１ＬＯ９０
この生成物を加熱融解後、減圧下で蒸留して沸点１５９
℃７２．５ ｍ Ｂｙの留分１Ｑ、７ｆ′ｔ−得た。Hydrogen bromide gas generated little by little over 9 hours was blown into the reactor using 527 ml of bromine and 178 ml of bromine. After the reaction mixture was allowed to cool, ice water was added thereto, and 1,000 ml of ethyl ether was added thereto for extraction. The organic layer was washed with an aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, and the solvent was distilled off to obtain a crude product as white crystals. 1LO90 After heating and melting this product, it was distilled under reduced pressure to a boiling point of 159
Fraction 1Q, 7f't- was obtained at 72.5 mBy.
放置により結晶化した。融点８５．５〜Ｂ＆５℃。It crystallized upon standing. Melting point 85.5~B&5°C.
（文献値融点８＆５〜８７．５℃）。(Literature value melting point 8&5-87.5°C).
特許出願人 日産化学工業株式会社Patent applicant: Nissan Chemical Industries, Ltd.
Claims (1)
させること全特徴とする２−ブロム−６−フェノキシビ
リジンの製造方法。1. A method for producing 2-bromo-6-phenoxyviridine, which comprises reacting 2-chloro-6-phenoxyviridine with hydrogen bromide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56116658A JPS5818360A (en) | 1981-07-25 | 1981-07-25 | Preparation of 2-bromo-6-phenoxypyridine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56116658A JPS5818360A (en) | 1981-07-25 | 1981-07-25 | Preparation of 2-bromo-6-phenoxypyridine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5818360A true JPS5818360A (en) | 1983-02-02 |
Family
ID=14692685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56116658A Pending JPS5818360A (en) | 1981-07-25 | 1981-07-25 | Preparation of 2-bromo-6-phenoxypyridine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5818360A (en) |
-
1981
- 1981-07-25 JP JP56116658A patent/JPS5818360A/en active Pending
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