JP2572501B2 - Method for producing 2-fluoroisobutyric acid ester - Google Patents
Method for producing 2-fluoroisobutyric acid esterInfo
- Publication number
- JP2572501B2 JP2572501B2 JP4068751A JP6875192A JP2572501B2 JP 2572501 B2 JP2572501 B2 JP 2572501B2 JP 4068751 A JP4068751 A JP 4068751A JP 6875192 A JP6875192 A JP 6875192A JP 2572501 B2 JP2572501 B2 JP 2572501B2
- Authority
- JP
- Japan
- Prior art keywords
- acid ester
- reaction
- hydrogen fluoride
- acid
- fluoroisobutyric
- 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
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
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は、２−フルオロイソ酪酸
エステルの製造方法に関する。本発明により得られる２
−フルオロイソ酪酸エステルは、トリアジン系除草剤の
中間体として有用である。The present invention relates to a method for producing 2-fluoroisobutyric acid ester. 2 obtained by the present invention
-Fluoroisobutyrate is useful as an intermediate for triazine herbicides.
【０００２】[0002]
【従来の技術】トリアジン系除草剤として、国際公開公
報ＷＯ９０／０９３７８号には、例えば式BACKGROUND OF THE INVENTION As triazine herbicides, WO 90/09378 discloses, for example, compounds of the formula
【化１】 で示されるように、フェノキシアルキルアミノ基がトリ
アジン環に置換されたトリアジン系除草剤が開示されて
おり、同公報によれば、このトリアジン系除草剤は、除
草効果に優れているとともに水稲に対して薬害がないと
いう顕著な利点を有することが記載されている。Embedded image As shown in the above, a triazine herbicide in which a phenoxyalkylamino group is substituted on a triazine ring is disclosed.According to the publication, the triazine herbicide has excellent herbicidal effects and is effective against rice. It has a remarkable advantage of no phytotoxicity.
【０００３】この種のフェノキシアルキルアミノ基置換
トリアジン系除草剤は、例えば２−フルオロイソ酪酸エ
ステルに２−フェノキシ−１−メチル−エチルビグアニ
ドを反応させることにより得られる。そしてこの反応に
用いられる２−フルオロイソ酪酸エステルの製造方法と
して、Ｊ．Ｏｒｇ．Ｃｈｅｍ．３３ ４２７９（１９６
８）には、２−ブロモイソ酪酸エステルにＡｇＦを作用
させてハロゲン交換反応により２−フルオロイソ酪酸エ
ステルを得る方法が開示されている。この方法を反応式
で示すと以下の通りである。[0003] This kind of phenoxyalkylamino group-substituted triazine herbicide is obtained, for example, by reacting 2-fluoroisobutyric acid ester with 2-phenoxy-1-methyl-ethylbiguanide. A method for producing 2-fluoroisobutyric acid ester used in this reaction is described in J. Am. Org. Chem. 33 4279 (196
8) discloses a method of reacting 2-bromoisobutyrate with AgF to obtain a 2-fluoroisobutyrate by a halogen exchange reaction. This method is represented by the following reaction formula.
【０００４】[0004]
【化２】 ２−フルオロイソ酪酸エステルを製造するための他の方
法として、Ｊ．Ｏｒｇ．Ｃｈｅｍ．５５ ３４２３（１
９９０）には、イソ酪酸メチルエステルにリチウムジイ
ソプロピルアミン（ＬＤＡ）存在下トリメチルシリルク
ロライドを反応させて１−メトキシ−１−（トリメチル
シリルオキシ）−２−メチルプロペンを得、次いでこれ
にＣＦＣｌ3 中Ｆ2 を反応させて２−フルオロイソ酪酸
エステルを得る方法が開示されている。この方法を反応
式で示すと以下の通りである。Embedded image Other methods for producing 2-fluoroisobutyric acid esters are described in Org. Chem. 55 3423 (1
990), by reacting isobutyric acid methyl ester with trimethylsilyl chloride in the presence of lithium diisopropylamine (LDA) to obtain 1-methoxy-1- (trimethylsilyloxy) -2-methylpropene, which is then added to F 2 in CFCl 3. To obtain 2-fluoroisobutyric acid ester. This method is represented by the following reaction formula.
【０００５】[0005]
【化３】 Embedded image
【０００６】[0006]
【発明が解決しようとする課題】しかし２−ブロモイソ
酪酸エステルを原料とする上記従来技術の方法は、２−
ブロモイソ酪酸エステルから２−フルオロイソ酪酸エス
テルを製造する工程においてメタクリル酸エステルが副
生するので、目的物質の２−フルオロイソ酪酸エステル
の収率が低いという欠点があった。またハロゲン交換反
応のための反応試薬であるＡｇＦが高価であり、製造コ
ストが高くなるという欠点もあった。またイソ酪酸メチ
ルエステルを原料とする上記従来技術の方法は、２工程
反応であり、目的物の収率が低下するという欠点があっ
た。また第１工程および第２工程の反応が−７８℃とい
う極低温で行なわなければならず、冷凍機等の特別な設
備が必要であるという欠点もあった。従って本発明の目
的は、２−フルオロイソ酪酸エステルを簡易な設備で高
収率かつ安価に製造することができる方法を提供するこ
とにある。However, the above-mentioned prior art method using 2-bromoisobutyric acid ester as a raw material involves the following two steps.
In the process of producing 2-fluoroisobutyric acid ester from bromoisobutyric acid ester, methacrylic acid ester is produced as a by-product, so that the yield of the target substance, 2-fluoroisobutyric acid ester, is low. Further, AgF, which is a reaction reagent for the halogen exchange reaction, is expensive, and there is a disadvantage that the production cost is increased. Further, the above-mentioned conventional method using isobutyric acid methyl ester as a raw material is a two-step reaction, and has a drawback that the yield of the target product is reduced. In addition, there is a disadvantage that the reactions of the first step and the second step must be performed at an extremely low temperature of -78 ° C, and special equipment such as a refrigerator is required. Accordingly, an object of the present invention is to provide a method capable of producing 2-fluoroisobutyric acid ester with a simple facility at a high yield and at a low cost.
【０００７】[0007]
【課題を解決するための手段】本発明者らは、（１）２
−ヒドロキシイソ酪酸エステルにフルオロ硫酸をフッ化
水素源の不存在下または存在下に反応させることによ
り、または（２）２−ヒドロキシイソ酪酸エステルにク
ロロ硫酸をフッ化水素源の存在下に反応させることによ
り、２−フルオロイソ酪酸エステルを、簡易な設備で高
収率かつ安価に製造することができることを見い出し、
この知見に基づき本発明を完成した。従って本発明は、
２−ヒドロキシイソ酪酸エステルにフルオロ硫酸をフッ
化水素源の不存在下または存在下に反応させることを特
徴とする２−フルオロイソ酪酸エステルの製造方法を要
旨とするものである。また本発明は、２−ヒドロキシイ
ソ酪酸エステルにクロロ硫酸をフッ化水素源の存在下に
反応させることを特徴とする２−フルオロイソ酪酸エス
テルの製造方法を要旨とするものである。Means for Solving the Problems The present inventors have proposed (1) 2
-Reacting fluorosulfuric acid with hydroxyisobutyrate in the absence or presence of a hydrogen fluoride source, or (2) reacting chlorosulfuric acid with 2-hydroxyisobutyrate in the presence of a hydrogen fluoride source Thereby, it has been found that 2-fluoroisobutyric acid ester can be produced at a high yield and at a low cost with simple equipment,
The present invention has been completed based on this finding. Therefore, the present invention
A gist of the present invention is a method for producing 2-fluoroisobutyric acid ester, which comprises reacting 2-hydroxyisobutyric acid ester with fluorosulfuric acid in the absence or presence of a hydrogen fluoride source. The present invention also provides a method for producing 2-fluoroisobutyric acid ester, which comprises reacting chlorosulfuric acid with 2-hydroxyisobutyric acid ester in the presence of a hydrogen fluoride source.
【０００８】以下、本発明を詳述する。本発明の２−フ
ルオロイソ酪酸エステルの製造方法において出発物質と
して用いられる２−ヒドロキシイソ酪酸エステルとして
は、例えば一般式（Ｉ）Hereinafter, the present invention will be described in detail. The 2-hydroxyisobutyric acid ester used as a starting material in the method for producing 2-fluoroisobutyric acid ester of the present invention includes, for example, a compound represented by the general formula (I)
【化４】 （式中、Ｒは低級アルキル基である）で示される２−ヒ
ドロキシイソ酪酸エステルが挙げられる。この２−ヒド
ロキシイソ酪酸エステルを示す一般式（Ｉ）において、
Ｒの低級アルキル基としては、メチル基、エチル基、ｎ
−プロピル基、ｉ−プロピル基、ｎ−ブチル基、ｉ−ブ
チル基、ｓｅｃ−ブチル基、ｔ−ブチル基が挙げられ
る。本発明によれば、（１）前記の２−ヒドロキシイソ
酪酸エステルにフルオロ硫酸をフッ化水素源の不存在下
または存在下に反応させることにより、また（２）前記
の２−ヒドロキシイソ酪酸エステルにクロロ硫酸をフッ
化水素源の存在下に反応させることにより、２−フルオ
ロイソ酪酸エステルが得られる。Embedded image (Wherein R is a lower alkyl group). In the general formula (I) showing this 2-hydroxyisobutyric acid ester,
As the lower alkyl group for R, a methyl group, an ethyl group, n
-Propyl group, i-propyl group, n-butyl group, i-butyl group, sec-butyl group and t-butyl group. According to the present invention, (1) the above-mentioned 2-hydroxyisobutyrate is reacted with fluorosulfuric acid in the absence or presence of a hydrogen fluoride source; Is reacted with chlorosulfuric acid in the presence of a hydrogen fluoride source to obtain 2-fluoroisobutyric acid ester.
【０００９】すなわち、２−ヒドロキシイソ酪酸エステ
ルと反応する試剤としてフルオロ硫酸を用いた場合は、
フッ化水素源を存在させなくても２−ヒドロキシイソ酪
酸エステルを得ることができるが、フッ化水素源を存在
させることにより反応時間の短縮、収率の向上という利
点が得られる。一方クロロ硫酸を用いた場合には、フッ
化水素源の存在は必須である。フッ化水素源としては、
無水フッ化水素、アミン類を０ｗｔ％を超えて含み、特
に１〜５０ｗｔ％含むフッ化水素などが用いられる。上
記アミン類の含有量は５ｗｔ％以下であるのが好まし
い。なお、上記アミン類としては、ピリジン、メラミ
ン、コリジンなどの芳香族アミンや、トリメチルアミ
ン、トリエチルアミン、トリブチルアミンなどの第３級
脂肪族アミンなどが挙げられる。上記フッ化水素源は、
反応時にフッ化水素の状態にあれば良く、従ってフッ化
水素前駆体を反応系に仕込み、反応系内でフッ化水素を
生成させても良い。なお、フルオロ硫酸やクロロ硫酸
は、原料１モルに対して１モル以上、好ましくは１．５
〜１０モル用いればよい。反応温度は臨界的ではないが
０〜７０℃、特に１０〜５０℃が好ましい。また反応圧
力も臨界的ではなく、常圧反応および加圧反応のいずれ
も採用できる。◎以上述べた本発明の方法によれば、２
−ヒドロキシイソ酪酸エステルから２−フルオロイソ酪
酸エステルを簡易な設備で高収率かつ安価に得ることが
できるので、その工業的意義は極めて大きい。That is, when fluorosulfuric acid is used as a reagent that reacts with 2-hydroxyisobutyric acid ester,
Although 2-hydroxyisobutyric acid ester can be obtained without the presence of a hydrogen fluoride source, the presence of the hydrogen fluoride source has the advantage of shortening the reaction time and improving the yield. On the other hand, when chlorosulfuric acid is used, the presence of a hydrogen fluoride source is essential. As a hydrogen fluoride source,
Hydrogen fluoride containing anhydrous hydrogen fluoride and amines in an amount exceeding 0 wt%, particularly 1 to 50 wt% is used. The content of the amines is preferably 5 wt% or less. Examples of the amines include aromatic amines such as pyridine, melamine, and collidine, and tertiary aliphatic amines such as trimethylamine, triethylamine, and tributylamine. The hydrogen fluoride source,
It suffices if it is in a state of hydrogen fluoride at the time of the reaction. Therefore, a hydrogen fluoride precursor may be charged into the reaction system to generate hydrogen fluoride in the reaction system. The amount of fluorosulfuric acid or chlorosulfuric acid is not less than 1 mol, preferably 1.5 mol per mol of the raw material.
It may be used in an amount of 10 to 10 mol. The reaction temperature is not critical, but is preferably from 0 to 70C, particularly preferably from 10 to 50C. Also, the reaction pressure is not critical, and either normal pressure reaction or pressure reaction can be employed. ◎ According to the method of the present invention described above, 2
Since 2-fluoroisobutyric acid ester can be obtained from -hydroxyisobutyric acid ester with a simple facility at a high yield and at a low cost, its industrial significance is extremely large.
【００１０】[0010]
【実施例】以下、実施例により本発明をさらに説明する
が、本発明はこれらの実施例に限定されるものではな
い。 実施例１ テフロン製反応容器にフルオロ硫酸８．２ｇ（８２．０
mM）を入れ、０℃に冷却後、撹拌しながら２−ヒドロキ
シイソ酪酸メチル４．８ｇ（４０．７mM）を３０分かけ
て加えた。０℃で１時間撹拌した後、室温（２０℃）に
戻し、６０時間撹拌した。反応終了後、反応混合物を氷
水中に注ぎ込み、塩化メチレンで抽出した。塩化メチレ
ン抽出液を無水硫酸ナトリウムで乾燥した後、塩化メチ
レンを減圧下に留去し、蒸留して沸点７０℃（１５０mm
Hg）の２−フルオロイソ酪酸メチル０．９３ｇ（収率１
９％）を得た。EXAMPLES The present invention will be further described below with reference to examples, but the present invention is not limited to these examples. Example 1 8.2 g of fluorosulfuric acid (82.0
mM) and cooled to 0 ° C., and 4.8 g (40.7 mM) of methyl 2-hydroxyisobutyrate was added over 30 minutes while stirring. After stirring at 0 ° C. for 1 hour, the mixture was returned to room temperature (20 ° C.) and stirred for 60 hours. After completion of the reaction, the reaction mixture was poured into ice water and extracted with methylene chloride. After the methylene chloride extract was dried over anhydrous sodium sulfate, the methylene chloride was distilled off under reduced pressure and distilled to a boiling point of 70 ° C. (150 mm
Hg) 0.93 g of methyl 2-fluoroisobutyrate (yield 1
9%).
【００１１】実施例２ テフロン製内筒を有する５０mlオートクレーブに、９ml
のフッ化水素（ＨＦ）／ピリジン（Ｐｙ）混合物（ＨＦ
／Ｐｙ＝７０／３０（ｗｔ／ｗｔ）であり、フッ化水素
を約３００mM含む）と、９．１５ｇ（９１．５mM）のフ
ルオロ硫酸とを入れ０℃に冷却した。３．６ｇ（３０．
５mM）の２−ヒドロキシイソ酪酸メチルを加えた後、４
０℃に加熱し４時間反応させた。反応終了後、反応混合
物を氷水中に注ぎ込み、塩化メチレンで抽出した。塩化
メチレン抽出液を無水硫酸ナトリウムで乾燥した後、減
圧下に塩化メチレンを留去し、蒸留して沸点７０℃（１
５０mmHg））の２−フルオロイソ酪酸メチル１９ｇ（収
率５２％）を得た。得られた２−フルオロイソ酪酸メチ
ルの常圧における沸点は１０６〜１０７℃であった。Example 2 In a 50 ml autoclave having a Teflon inner cylinder, 9 ml
Hydrogen fluoride (HF) / pyridine (Py) mixture (HF
/ Py = 70/30 (wt / wt), containing about 300 mM hydrogen fluoride) and 9.15 g (91.5 mM) of fluorosulfuric acid, and cooled to 0 ° C. 3.6 g (30.
5 mM) of methyl 2-hydroxyisobutyrate,
The mixture was heated to 0 ° C. and reacted for 4 hours. After completion of the reaction, the reaction mixture was poured into ice water and extracted with methylene chloride. After the methylene chloride extract was dried over anhydrous sodium sulfate, methylene chloride was distilled off under reduced pressure, and the residue was distilled to a boiling point of 70 ° C. (1 ° C.).
19 g of methyl 2-fluoroisobutyrate (50 mmHg)) were obtained (yield: 52%). The boiling point of the obtained methyl 2-fluoroisobutyrate at normal pressure was 106 to 107 ° C.
【００１２】実施例３〜６ フルオロ硫酸の量、フッ化水素源（ＨＦ／Ｐｙ＝７０／
３０（wt／wt）の混合物）の量、反応温度および反応時
間を変えた以外は実施例２と同様に実施して２−フルオ
ロイソ酪酸メチルを得た。 実施例７ フルオロ硫酸の量を変え、フッ化水素源としてＨＦ／Ｐ
ｙ混合物（９５／５（wt／wt））を用い、さらに反応温
度および反応時間を変えた以外は実施例２と同様に実施
して２−フルオロイソ酪酸メチルを得た。Examples 3 to 6 Amount of fluorosulfuric acid, hydrogen fluoride source (HF / Py = 70 /
30 (wt / wt) mixture, the reaction temperature and the reaction time were changed, except that the reaction was carried out in the same manner as in Example 2 to obtain methyl 2-fluoroisobutyrate. Example 7 The amount of fluorosulfuric acid was changed, and HF / P was used as a hydrogen fluoride source.
Using y mixture (95/5 (wt / wt)), the reaction was carried out in the same manner as in Example 2 except that the reaction temperature and the reaction time were changed, to obtain methyl 2-fluoroisobutyrate.
【００１３】実施例８〜９ フルオロ硫酸の量を変え、フッ化水素源として無水ＨＦ
を用い、さらに反応温度および反応時間を変えた以外は
実施例２と同様に実施して２−フルオロイソ酪酸メチル
を得た。Examples 8 to 9 The amount of fluorosulfuric acid was changed and anhydrous HF was used as a hydrogen fluoride source.
And the reaction was carried out in the same manner as in Example 2 except that the reaction temperature and the reaction time were changed to obtain methyl 2-fluoroisobutyrate.
【００１４】実施例１０〜１１ フルオロ硫酸の代りにクロロ硫酸を用い、表２に示した
条件以外は実施例２と同様に実施して２−フルオロイソ
酪酸メチルを得た。Examples 10 to 11 Methyl 2-fluoroisobutyrate was obtained in the same manner as in Example 2 except that chlorosulfuric acid was used instead of fluorosulfuric acid, except for the conditions shown in Table 2.
【００１５】実施例１２〜１３ ２−ヒドロキシイソ酪酸メチルの代りに２−ヒドロキシ
イソ酪酸エチルを用い、表２に示した条件以外は実施例
２と同様にして２−フルオロイソ酪酸エチルを得た。得
られた２−フルオロイソ酪酸エチルの常圧における沸点
は、１２４〜１２６℃であった。Examples 12 to 13 Ethyl 2-fluoroisobutyrate was obtained in the same manner as in Example 2 except that ethyl 2-hydroxyisobutyrate was used in place of methyl 2-hydroxyisobutyrate. The boiling point of the obtained ethyl 2-fluoroisobutyrate at normal pressure was 124 to 126 ° C.
【００１６】実施例１４ フルオロ硫酸の代りにクロロ硫酸を用いた以外は実施例
１２と同様にして２−フルオロイソ酪酸エチルを得た。Example 14 Ethyl 2-fluoroisobutyrate was obtained in the same manner as in Example 12 except that chlorosulfuric acid was used instead of fluorosulfuric acid.
【００１７】上記実施例１〜１４の反応条件および結果
は表１および表２に示した。The reaction conditions and results of Examples 1 to 14 are shown in Tables 1 and 2.
【００１８】[0018]
【表１】 [Table 1]
【００１９】[0019]
【表２】 表１より明らかなように、出発原料として２−ヒドロキ
シイソ酪酸メチルを用い、反応試剤としてフルオロ硫酸
を用いた場合、フッ化水素源が存在しなくても室温で反
応が進行し２−フルオロイソ酪酸メチルを得ることがで
きた（実施例１）。またフルオロ硫酸とともにフッ化水
素源（HF/Py 又は無水HF）を用いると、高収率で２−フ
ルオロイソ酪酸メチルを得ることができた（実施例２〜
９）。さらにフルオロ硫酸の代りにクロロ硫酸を用い、
フッ化水素源（HF/Py ）の存在下に反応を行なっても、
高収率の２−フルオロイソ酪酸メチルを得ることができ
た（実施例１０〜１１）。また出発原料として２−ヒド
ロキシイソ酪酸エチルを用いた場合にも高収率で２−フ
ルオロイソ酪酸エチルを得ることができた（実施例１２
〜１４）。[Table 2] As is clear from Table 1, when methyl 2-hydroxyisobutyrate is used as a starting material and fluorosulfuric acid is used as a reaction reagent, the reaction proceeds at room temperature without the presence of a hydrogen fluoride source, and 2-fluoroisobutyric acid is produced. Methyl could be obtained (Example 1). When a hydrogen fluoride source (HF / Py or anhydrous HF) was used together with fluorosulfuric acid, methyl 2-fluoroisobutyrate could be obtained in high yield (Examples 2 to 4).
9). Using chlorosulfuric acid instead of fluorosulfuric acid,
Even if the reaction is performed in the presence of a hydrogen fluoride source (HF / Py),
A high yield of methyl 2-fluoroisobutyrate could be obtained (Examples 10 to 11). In addition, even when ethyl 2-hydroxyisobutyrate was used as a starting material, ethyl 2-fluoroisobutyrate could be obtained in high yield (Example 12).
To 14).
【００２０】[0020]
【発明の効果】以上述べたように、本発明によれば、２
−フルオロイソ酪酸エステルを簡易な設備で高収率かつ
安価に製造することができる方法が提供された。As described above, according to the present invention, 2
-A method has been provided in which fluoroisobutyric acid ester can be produced in a simple facility with high yield and at low cost.
Claims (2)
オロ硫酸をフッ化水素源の不存在下または存在下に反応
させることを特徴とする２−フルオロイソ酪酸エステル
の製造方法。1. A method for producing 2-fluoroisobutyric acid ester, comprising reacting 2-hydroxyisobutyric acid ester with fluorosulfuric acid in the absence or presence of a hydrogen fluoride source.
ロ硫酸をフッ化水素源の存在下に反応させることを特徴
とする２−フルオロイソ酪酸エステルの製造方法。2. A process for producing 2-fluoroisobutyric acid ester, comprising reacting 2-hydroxyisobutyric acid ester with chlorosulfuric acid in the presence of a hydrogen fluoride source.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4068751A JP2572501B2 (en) | 1991-03-27 | 1992-03-26 | Method for producing 2-fluoroisobutyric acid ester |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6311491 | 1991-03-27 | ||
| JP3-63114 | 1991-03-27 | ||
| JP4068751A JP2572501B2 (en) | 1991-03-27 | 1992-03-26 | Method for producing 2-fluoroisobutyric acid ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0585987A JPH0585987A (en) | 1993-04-06 |
| JP2572501B2 true JP2572501B2 (en) | 1997-01-16 |
Family
ID=26404198
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4068751A Expired - Lifetime JP2572501B2 (en) | 1991-03-27 | 1992-03-26 | Method for producing 2-fluoroisobutyric acid ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2572501B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994024086A1 (en) * | 1993-04-08 | 1994-10-27 | Idemitsu Kosan Co., Ltd. | Process for producing 2-fluoroisobutyric acid or ester thereof |
| JP5600994B2 (en) * | 2010-03-29 | 2014-10-08 | セントラル硝子株式会社 | Method for producing 2-fluoroisobutyric acid ester |
-
1992
- 1992-03-26 JP JP4068751A patent/JP2572501B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0585987A (en) | 1993-04-06 |
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