JPH0160458B2 - - Google Patents
Info
- Publication number
- JPH0160458B2 JPH0160458B2 JP60145383A JP14538385A JPH0160458B2 JP H0160458 B2 JPH0160458 B2 JP H0160458B2 JP 60145383 A JP60145383 A JP 60145383A JP 14538385 A JP14538385 A JP 14538385A JP H0160458 B2 JPH0160458 B2 JP H0160458B2
- Authority
- JP
- Japan
- Prior art keywords
- copper
- reaction
- mol
- fluoride
- present
- 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
Links
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、ハロゲン交換反応等によるフルオロ
有機化合物の製法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for producing a fluoroorganic compound by halogen exchange reaction or the like.
従来、金属フツ化物をフツ素化剤にして、ハロ
ゲン交換反応で有機フツ化物を合成することはよ
く行われている〔例えば、ジヤーナル・オブ・
ザ・アメリカン・ケミカル・ソサエテイー79巻
2311頁（1957）、同誌96巻2250頁（1974）、シンセ
シス428頁（1974）、同誌427頁（1976）、ケミスト
リーレターズ761頁（1981）参照〕が、いずれも
反応温度が高く反応時間も長いので、副反応でオ
レフインが生成しやすく、目的物の収率は低かつ
た。
Conventionally, it has been common practice to synthesize organic fluorides through halogen exchange reactions using metal fluorides as fluorinating agents [for example, Journal of
The American Chemical Society Volume 79
2311 (1957), Volume 96, page 2250 (1974), Synthesis, page 428 (1974), Volume 427 (1976), Chemistry Letters, page 761 (1981)], but the reaction temperature is high and the reaction time is long. Therefore, olefins were likely to be produced as a side reaction, and the yield of the target product was low.
最近、一価または二価のフツ化銅と有機臭化物
または塩化物を含窒素化合物の存在下反応させる
と、温和な反応条件でハロゲン交換反応が起こ
り、有機フツ化物が収率よく得られることがわか
つた〔日本化学会第49春季年会 講演予稿集
1H17917頁および1Y07 1476頁参照〕。 Recently, it has been reported that when monovalent or divalent copper fluoride is reacted with an organic bromide or chloride in the presence of a nitrogen-containing compound, a halogen exchange reaction occurs under mild reaction conditions, and the organic fluoride can be obtained in good yield. Wakatsuta [Chemical Society of Japan 49th Spring Annual Meeting Proceedings]
See pages 1H17917 and 1Y07 1476].
本発明者らは、温和な条件のハロゲン交換反応
によるフツ化物の製法についてさらに検討し、本
発明に到達した。 The present inventors further investigated a method for producing a fluoride using a halogen exchange reaction under mild conditions, and arrived at the present invention.
本発明の目的は、反応条件が温和でオレフイン
の副生がほとんどない、収率のよいフルオロ有機
化合物の製法を提供することである。
An object of the present invention is to provide a method for producing a fluoroorganic compound with mild reaction conditions, with almost no olefin by-product, and with a good yield.
本発明の要旨は、一般式：
Ｒ―Ｘ
（式中、Ｒはアルキル基、Ｘは塩素、臭素、沃
素または―OTs基〔但し、Tsはトシル基であ
る。〕を示す。）
で表される有機化合物、フツ化銅（）および銅
を、ｒ―コリジンまたは２，2'―ビピリジルの存
在下反応させることからなる、一般式：
Ｒ―Ｆ
（式中、Ｒは前記と同じ。）
で表わされるフルオロ有機化合物の製法に存す
る。
The gist of the present invention is the general formula: R-X (wherein R is an alkyl group, and X is chlorine, bromine, iodine, or -OTs group [provided, Ts is a tosyl group]). The general formula consists of reacting the represented organic compound, copper fluoride () and copper in the presence of r-collidine or 2,2'-bipyridyl: RF (wherein R is the same as above). ) consists in a method for producing a fluoroorganic compound represented by
上記アルキル基の具体例としては、C8H17-が
挙げられるがこれに限定されない。 Specific examples of the alkyl group include, but are not limited to, C 8 H 17- .
上記原料有機化合物とフツ化銅（）の仕込モ
ル比は、原料有機化合物１モルに対し通常フツ化
銅（）１〜５モル、好ましくは１〜２モルであ
る。 The molar ratio of the raw material organic compound to copper fluoride () is usually 1 to 5 mol, preferably 1 to 2 mol, per 1 mol of the raw material organic compound.
フツ化銅（）と銅の仕込モル比は、フツ化銅
（）１モルに対し通常銅0.5〜2.0モル、好まし
しくは0.8〜1.5モルである。 The molar ratio of copper fluoride () to copper is usually 0.5 to 2.0 mol, preferably 0.8 to 1.5 mol, of copper per 1 mol of copper fluoride ().
上記原料有機化合物とｒ―コリジンまたは２，
2′―ビピリジルの仕込モル比は、原料有機化合物
１モルに対し通常ｒ―コリジンまたは２，2′―ビ
ピリジル１〜５モル、好ましくは２〜３モルであ
る。 The above raw material organic compound and r-collidine or 2,
The molar ratio of 2'-bipyridyl to be charged is usually 1 to 5 mol, preferably 2 to 3 mol, of r-collidine or 2,2'-bipyridyl per 1 mol of the starting organic compound.
本発明の反応の反応温度は、通常90〜160℃、
好ましくは120〜140℃である。 The reaction temperature of the reaction of the present invention is usually 90 to 160°C,
Preferably it is 120-140°C.
本発明の反応の反応時間は、通常0.5〜１時間
である。 The reaction time of the reaction of the present invention is usually 0.5 to 1 hour.
実施例 １
50cm3のナス型フラスコにｎ―C8H17Br 0.966ｇ
（5mmo）、フツ化銅（）0.660ｇ（6.5mmo
）、銅0.413ｇ（6.5mmo）および２，2′―ビ
ピリジル2.030ｇ（13mmo）を入れ、アルゴン
雰囲気中、130℃で45分間反応を行つた。原料の
転化率は100％で、フツ素置換体の収率は75％で
あつた。
Example 1 0.966 g of n-C 8 H 17 Br in a 50 cm 3 eggplant-shaped flask
(5 mmo), copper fluoride () 0.660 g (6.5 mmo)
), 0.413 g (6.5 mmo) of copper, and 2.030 g (13 mmo) of 2,2'-bipyridyl were added, and a reaction was carried out at 130° C. for 45 minutes in an argon atmosphere. The conversion rate of the raw material was 100%, and the yield of the fluorine-substituted product was 75%.
実施例 ２
50cm3のナス型フラスコにｎ―C8H17Br 0.966ｇ
（5mmol）、フツ化銅（）0.660ｇ（6.5mmol）、
銅0.413ｇ（6.5mmol）およびｒ―コリジン2.747
ｇ（22.7mmol）を入れ、アルゴン雰囲気中、130
℃で45分間反応を行つた。原料の転化率は97％
で、フツ素置換体の収率は75％であつた。Example 2 0.966 g of n-C 8 H 17 Br in a 50 cm 3 eggplant-shaped flask
(5mmol), copper fluoride () 0.660g (6.5mmol),
Copper 0.413g (6.5mmol) and r-collidine 2.747
g (22.7 mmol) in an argon atmosphere at 130
The reaction was carried out at ℃ for 45 minutes. Conversion rate of raw material is 97%
The yield of the fluorine-substituted product was 75%.
比較例
銅を使用しなかつた他は、実施例と同様の手順
で反応を行つた。原料の転化率は32％で、フツ素
置換体はその内の63％しかなかつた。Comparative Example A reaction was carried out in the same manner as in the example except that copper was not used. The conversion rate of the raw material was 32%, of which only 63% was fluorinated.
本発明の製法によれば、温和な反応条件で収率
よくフツ素置換体を得ることができる。
According to the production method of the present invention, a fluorine-substituted product can be obtained in good yield under mild reaction conditions.
Claims (1)
素または―OTs基〔但し、Tsはトシル基であ
る。〕を示す。） で表される有機化合物、フツ化銅（）および銅
を、ｒ―コリジンまたは２，2'―ビピリジルの存
在下反応させることからなる、一般式： Ｒ―Ｆ （式中、Ｒは前記と同じ。） で表わされるフルオロ有機化合物の製法。[Claims] 1 General formula: R-X (wherein, R is an alkyl group, and X is chlorine, bromine, iodine, or -OT s group [provided, T s is a tosyl group]) A general formula consisting of reacting an organic compound represented by, copper fluoride () and copper in the presence of r-collidine or 2,2'-bipyridyl: .) A method for producing a fluoroorganic compound represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60145383A JPS625929A (en) | 1985-07-02 | 1985-07-02 | Method for producing fluoroorganic compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60145383A JPS625929A (en) | 1985-07-02 | 1985-07-02 | Method for producing fluoroorganic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS625929A JPS625929A (en) | 1987-01-12 |
| JPH0160458B2 true JPH0160458B2 (en) | 1989-12-22 |
Family
ID=15383972
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60145383A Granted JPS625929A (en) | 1985-07-02 | 1985-07-02 | Method for producing fluoroorganic compounds |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS625929A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69711428T2 (en) * | 1996-12-27 | 2002-10-31 | Daikin Industries, Ltd. | METHOD FOR PRODUCING PERFLUORAL KANES AND IODINE PENTAFLUORIDES |
| US7202388B2 (en) * | 2004-10-06 | 2007-04-10 | E. I. Du Pont De Nemours And Company | Processes for preparing fluoroarenes from haloarenes |
-
1985
- 1985-07-02 JP JP60145383A patent/JPS625929A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS625929A (en) | 1987-01-12 |
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