JPS63107945A - Production of perfluorohexylmethylbenzene derivative - Google Patents
Production of perfluorohexylmethylbenzene derivativeInfo
- Publication number
- JPS63107945A JPS63107945A JP61254172A JP25417286A JPS63107945A JP S63107945 A JPS63107945 A JP S63107945A JP 61254172 A JP61254172 A JP 61254172A JP 25417286 A JP25417286 A JP 25417286A JP S63107945 A JPS63107945 A JP S63107945A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- methylpent
- ene
- perfluoro
- benzyl bromide
- 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
- SNKXXXAVLOQHKL-UHFFFAOYSA-N 1,2,3,4-tetrafluoro-5-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)-6-(trifluoromethyl)benzene Chemical class FC=1C(=C(C(=C(C=1F)F)F)C(F)(F)F)C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F SNKXXXAVLOQHKL-UHFFFAOYSA-N 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- FAEGGADNHFKDQX-UHFFFAOYSA-N 1,1,1,3,4,4,5,5,5-nonafluoro-2-(trifluoromethyl)pent-2-ene Chemical compound FC(F)(F)C(C(F)(F)F)=C(F)C(F)(F)C(F)(F)F FAEGGADNHFKDQX-UHFFFAOYSA-N 0.000 claims abstract description 10
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical class BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 claims abstract description 8
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 claims abstract description 6
- 229910001634 calcium fluoride Inorganic materials 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims abstract description 5
- 239000011698 potassium fluoride Substances 0.000 claims description 16
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 14
- 235000003270 potassium fluoride Nutrition 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 239000012025 fluorinating agent Substances 0.000 abstract description 4
- CKRNPRFOXFWMGH-UHFFFAOYSA-K calcium;potassium;trifluoride Chemical compound [F-].[F-].[F-].[K+].[Ca+2] CKRNPRFOXFWMGH-UHFFFAOYSA-K 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 238000006471 dimerization reaction Methods 0.000 abstract description 2
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003921 oil Substances 0.000 abstract description 2
- 239000004094 surface-active agent Substances 0.000 abstract description 2
- 230000005611 electricity Effects 0.000 abstract 1
- 239000010720 hydraulic oil Substances 0.000 abstract 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- JMMZCWZIJXAGKW-UHFFFAOYSA-N 2-methylpent-2-ene Chemical compound CCC=C(C)C JMMZCWZIJXAGKW-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000013024 sodium fluoride Nutrition 0.000 description 2
- 239000011775 sodium fluoride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000005172 methylbenzenes Chemical class 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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)
Abstract
Description
【発明の詳細な説明】
産業上の利用分野
本発明は界面活性剤の出発原料、並びに電気装置におけ
る絶縁油、精密機器に使用される不活性作動油として有
用なペルフルオロヘキシルメチルベンゼン誘導体の製造
法に関する。DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to a method for producing perfluorohexylmethylbenzene derivatives useful as starting materials for surfactants, insulating oils in electrical equipment, and inert hydraulic fluids used in precision instruments. Regarding.
従来技術
および
発明が解決しようとする問題点
ペルフルオロ−２−メチルペント−２−エンとベンジル
ブロマイドからペルフルオロヘキシルメチルベンゼンを
製造する方法は知られている［マカロフら（Ｋ、Ｎ、Ｍ
ＡＫＡＲＯＶ ｅｔ ａｌ）； ジャーナル・オン・フ
ルオライン・ケミストリー（Ｊｏａｒｎａｌ ｏｆ Ｆ
ｌｕｏｒｉｎｅ Ｃｈｅｍｉｓｔｒｙ）第１Ｏ巻、第１
５７頁〜第１５８頁（１９７７）参照コ。この合成法に
よれば、反応溶媒としてジグリムを使用し塩基性触媒と
してフッ化セシウムを使用することによって、室温、且
つ短時間て高収率でペルフルオロヘキシルメチルベンゼ
ンが得られる。PRIOR ART AND THE PROBLEM TO BE SOLVED BY THE INVENTION Processes for producing perfluorohexylmethylbenzene from perfluoro-2-methylpent-2-ene and benzyl bromide are known [Makarov et al.
AKAROV et al); Journal of Fluorine Chemistry
Luorine Chemistry) Volume 1O, Volume 1
See pages 57 to 158 (1977). According to this synthesis method, by using diglyme as a reaction solvent and cesium fluoride as a basic catalyst, perfluorohexylmethylbenzene can be obtained in high yield at room temperature and in a short time.
この反応は、次式のように中間状態として、ペルフルオ
ロ−ｔｅｒｔ−カルボアニオンを経由して進行すると考
えられている。This reaction is thought to proceed via perfluoro-tert-carbanion as an intermediate state as shown in the following formula.
しかしながら、フッ化セシウムは高価且つ非常に吸湿性
の強い化合物の為、実用的でｔ；い。フッ化セシウムの
かわりにＫＦ、ＮａＦを用いて上と同様の条件下でこの
反応を行っても、目的化合物は極端に低い収率でしか得
られない。これはフッ化ナトリウムやフッ化カリウムで
は、安定なカルボアニオンの生成が困難なために反応か
進行し難いものと考えられる。However, since cesium fluoride is an expensive and highly hygroscopic compound, it is not practical. Even if this reaction is carried out under the same conditions as above using KF or NaF instead of cesium fluoride, the target compound can only be obtained in an extremely low yield. This is thought to be because it is difficult for the reaction to proceed with sodium fluoride or potassium fluoride because it is difficult to generate stable carbanions.
この事は、従来、ヘキサフルオロオレフィン、又はテト
ラフルオロオレフィンの低分子量のオリゴマー（三量体
、三量体）のフッ素化剤としては、はとんどフッ化セシ
ウムに限られているという事実と対応する［例えば、特
開昭５７−１５０６２５号公報およびヤコブソンら（Ｇ
、Ｇ、ＹＡＫＯＩ３ＳＯＮ ｅｔ ａｌ、）； シン
セシス（Ｓ ｙｎｔｈｅｓｉｓ）第１６９頁（＋９８３
）参照］。This is due to the fact that conventionally, the fluorinating agent for low molecular weight oligomers (trimers, trimers) of hexafluoroolefins or tetrafluoroolefins has been limited to cesium fluoride. Corresponding [for example, Japanese Patent Application Laid-Open No. 57-150625 and Jacobson et al.
, G. YAKOI3SON et al.); Synthesis, page 169 (+983
)reference].
本発明者らは先に高価なＣｓＦの代わりにＫＦを使用し
、反応溶媒としてジグリムの代わりにジメチルホルムア
ミド（Ｄ Ｍ Ｐ ）を使用Ｖることによってペルフル
オロヘキシルメチルベンゼン誘導体が高収率で得られる
ことを究明した（特願昭６に７２２０６号参照）。The present inventors previously demonstrated that perfluorohexylmethylbenzene derivatives can be obtained in high yield by using KF instead of expensive CsF and using dimethylformamide (DMP) instead of diglyme as a reaction solvent. (See Japanese Patent Application No. 72206 in 1983).
しかしながらこの方法にも、一般に反応ＩｊｊＬ６が原
料のペルフルオロ−２−メチルペント−２−エンの沸点
よりも高く（約５０〜１５０℃、好ましくは約８０〜１
３０℃）、従って高価な密封反応容器等を必要とする等
の点で改良の余地か残されている。However, also in this method, the reaction IjjL6 is generally higher than the boiling point of the raw material perfluoro-2-methylpent-2-ene (about 50-150°C, preferably about 80-1
30°C), therefore, there is still room for improvement in that an expensive sealed reaction vessel is required.
本発明者は、上記の反応において、ハロゲン化アルキル
のフッ素化置換反応または幾つかの求核置換反応を温和
の条件下において良好な収率で進行さ什るＫＰ Ｃａ
Ｆ２試薬、即ちフッ化カルシウムの固体にフッ化カリウ
ムを担持させた試薬［例えば、イヂハラ（Ｉ ｃｈｉｈ
ａｒａ）ら、ジェー・ケム・ソス・、ケム・コミコン、
（Ｊ 、Ｃｈｅｍ、Ｓｏｃ、、 Ｃｈｅｍ。The present inventor has discovered that in the above reaction, KP Ca can be used to carry out the fluorination substitution reaction of alkyl halides or some nucleophilic substitution reactions under mild conditions with good yields.
F2 reagent, that is, a reagent in which potassium fluoride is supported on solid calcium fluoride [for example, Ichih
ara) et al., J.C.M.S.O., K.M.Comicon,
(J, Chem, Soc,, Chem.
Ｃｏｍｍｕｎ、）、 １９８６ 、第７９３頁〜第７９
４頁参照］をフッ素化剤として使用することによって、
室温〜５０°Ｃという低い反応温度においてらペルフル
オロヘキシルメチルベンゼン誘導体がｂｔ収率で得られ
ろことを究明して本発明を完成した。Commun, ), 1986, pp. 793-79
See page 4] as a fluorinating agent.
The present invention was completed by discovering that perfluorohexylmethylbenzene derivatives can be obtained in bt yield at a low reaction temperature of room temperature to 50°C.
問筈点を解決するための手段
即ち、本発明はペルフルオロ−２−メチルペント−２−
エンおよび一般式［Ｉ］：
（式中、ＲはＨｌｐ−ＣＮ、ｍ−ＣＮ、０−ＣＮ。Means for solving the problem, that is, the present invention provides perfluoro-2-methylpent-2-
ene and general formula [I]: (wherein R is Hlp-CN, m-CN, 0-CN.
ｐ−Ｎ０２、ｍＮ０ｔ、ｏ−Ｎｏ、、ｐ−Ｃ１−１２Ｂ
ｒまたはｍ ＣＩ（ｔ Ｂ ｒを表わす）で表わされ
るベンジルブロマイド誘導体をジメチルホルムアミド溶
媒中、フッ化カルシウムに担持させたフッ化カリウムの
存在下で反応させることを特徴とする、一般式［■］：
（式中、Ｒ′はト■、ｐ ＣＮ、ｍ ＣＮ、ｏ
ＣＮ１ｐＮＯ２、ｍＮＯ２，０−Ｎ０２、ｐ−ＣＨ６Ｒ
ｆまたはｍ ＣＨｔｎ ｒ基を表わし、
Ｆ３
ＲｆはＣＦ ３０ Ｆ 、ＣＦ ２Ｇ−基を表わす。）
□
Ｆ３
で表わされるペルフルオロヘキシルメチルベンゼン誘導
体の製造法に関する。p-N02, mN0t, o-No,, p-C1-12B
General formula [■] characterized by reacting a benzyl bromide derivative represented by r or m CI (representing tBr) in a dimethylformamide solvent in the presence of potassium fluoride supported on calcium fluoride : (In the formula, R' is g, p CN, m CN, o
CN1pNO2, mNO2,0-N02, p-CH6R
f or m CHtn represents a r group, and F3 Rf represents a CF 30 F, CF 2G- group. )
□Relates to a method for producing a perfluorohexylmethylbenzene derivative represented by F3.
ペルフルオロ−２−メチルペント−２−エンは例えばヘ
キサフルオロプロペンの２量化反応によって容易に得る
ことができる。Perfluoro-2-methylpent-2-ene can be easily obtained, for example, by dimerization reaction of hexafluoropropene.
本発明に使用するベンジルブロマイド誘導体としては、
前記一般式［１］において置換基Ｒが１−１．１）−Ｃ
Ｎ、ｍ−ＣＮ、ｏ−ＣＮ５ｐ−Ｎｏｔ、ｍ−Ｎｏｖ、Ｏ
ＮＯ！、ｐ−ＣＨ＊Ｂｒまたはｍ−ＣＩ−（ｔＢｒを表
わす化合物が例示される。The benzyl bromide derivatives used in the present invention include:
In the general formula [1], the substituent R is 1-1.1)-C
N, m-CN, o-CN5p-Not, m-Nov, O
NO! , p-CH*Br or m-CI-(tBr).
ペルフルオロ−２−メチルペント−２−エンとベンジル
ブロマイド誘導体との反応モル比は特に限定的ではない
が通常は前者１モルに対して後者的０５〜２モル、好ま
しくは約０５〜１モルである。The reaction molar ratio of perfluoro-2-methylpent-2-ene and benzyl bromide derivative is not particularly limited, but is usually 0.5 to 2 moles of the latter to 1 mole of the former, preferably about 0.5 to 1 mole.
本発明の特徴は前述のように、上記の反応をジメチルホ
ルムアミド溶媒中、フッ化カルシウムに担持さＵ′たフ
ッ化カリウム（Ｋ Ｆ −ＣａＦ ２）の存在下でおこ
なうことである。As mentioned above, the feature of the present invention is that the above reaction is carried out in a dimethylformamide solvent in the presence of potassium fluoride (K F -CaF 2 ) supported on calcium fluoride.
ＫＦ−ＣａＦ２は常法により、固体状のフッ化カルシウ
ムにフッ化カリウムを湿式法らしくは乾式法によって担
持し、加熱乾燥して調製すればよい。KF-CaF2 may be prepared by a conventional method by supporting potassium fluoride on solid calcium fluoride by a wet method or a dry method, and drying by heating.
フッ化カリウムの担持量は特に限定的ではないが、通常
はＫ Ｆ ／ ＣａＦ ｔ ＝ １ ／ １０〜ｌ ／
ｌ （重量比）である。Although the supported amount of potassium fluoride is not particularly limited, it is usually KF/CaFt=1/10~l/
l (weight ratio).
ＫＦ ＣａＦｔの使用量もＫＦの担持量等によって左
右され、特に限定的ではないか、通常はペルフルオロ−
２−メチルペント−２−エン１モルに対してＫＦが約１
〜３モル、好ましくはＩ−１゜５モルになるようにする
。The amount of KF CaFt used depends on the amount of KF supported, etc., and is not particularly limited.
KF is approximately 1 per mole of 2-methylpent-2-ene.
~3 moles, preferably I-1°5 moles.
本発明方法においては、フッ素化剤としてＫＦＣａ Ｐ
ｔを使用することによって上記の反応を原料であるペ
ルフルオロ−２−メチルペント−２−エンの沸点以下の
温度、即ち室温〜約５０℃でおこなうことができ、ペル
フルオロへキソルメヂルベンゼン誘導体の収率は従来法
に比べて遜色がないか、またはこれを凌駕する。もちろ
ん所望により上記反応をより高温、例えば約５０〜１０
０℃でおこなうこともできる。In the method of the present invention, KFCa P is used as a fluorinating agent.
By using t, the above reaction can be carried out at a temperature below the boiling point of the raw material perfluoro-2-methylpent-2-ene, that is, from room temperature to about 50°C, and the yield of perfluorohexol methylbenzene derivatives can be reduced. is comparable to or even superior to the conventional method. Of course, if desired, the above reaction may be carried out at higher temperatures, e.g.
It can also be carried out at 0°C.
以下、本発明を実施例によって説明する。Hereinafter, the present invention will be explained by examples.
夾嵐桝
ＫＰおよびＣａＦｔを重量比２・３で混合し、さらに少
量の蒸留水を添加して充分に撹拌混合した混合物を減圧
下での加熱乾燥処理に付してＫＦ−ＣａＦ、試薬を調製
した。Mix KP and CaFt at a weight ratio of 2.3, add a small amount of distilled water, and thoroughly stir and mix. The mixture is heated and dried under reduced pressure to prepare KF-CaF and a reagent. did.
ペルフルオロ−２−メチルペント−２−エン７゜５ ｇ
（２５ｍｍｏｌ）、臭化ベンジル３ 、０ ｍｆ２（２
５ｍｍｏｌ）および所定量の上記ＫＦ ＣａＦ２試薬
（ＫＦ５０ｍｍｏｌ含有）をジメチルホルムアミド３５
ｍ（２中に加え、充分に撹拌しながら反応を３５°０１
５０℃または７０℃で２４時間おこなった。生成した４
−［２，２−ビス（トリフルオロメチル）−３，３，４
゜４．５，５．５−ヘプタフルオロペンデル］ベンゼン
の収率をテトラリンを標学とするガスクロマトグラフィ
ーによって求めた。結果を以下の表−■に示す。Perfluoro-2-methylpent-2-ene 7°5 g
(25 mmol), benzyl bromide 3, 0 mf2 (2
5 mmol) and a predetermined amount of the above KF CaF2 reagent (containing 50 mmol of KF) in dimethylformamide 35
m (2) and stirred thoroughly to bring the reaction to 35°01
It was carried out at 50°C or 70°C for 24 hours. generated 4
-[2,2-bis(trifluoromethyl)-3,3,4
The yield of ゜4.5,5.5-heptafluoropendel]benzene was determined by gas chromatography using tetralin as a standard. The results are shown in the table below.
堆恰氏
ＫＦ ＣａＦｚ試薬の代りに、減圧下での加熱乾燥処
理に付したＫＦを使用する以外は実施例と同様にして反
応をおこなつｆ二。The reaction was carried out in the same manner as in Example f2, except that KF that had been subjected to heat drying treatment under reduced pressure was used instead of the KF CaFz reagent.
生成物の収率を以下の表−１に示す。The yield of the product is shown in Table 1 below.
表−１Table-1
Claims (1)
一般式［ I ］： ▲数式、化学式、表等があります▼［ I ］ （式中、ＲはＨ、ｐ−ＣＮ、ｍ−ＣＮ、ｏ−ＣＮ、ｐ−
ＮＯ＿２、ｍ−ＮＯ＿２、ｏ−ＮＯ＿２、ｐ−ＣＨ＿２
Ｂｒまたはｍ−ＣＨ＿２Ｂｒを表わす） で表わされるベンジルブロマイド誘導体をジメチルホル
ムアミド溶媒中、フッ化カルシウムに担持させたフッ化
カリウムの存在下で反応させることを特徴とする、一般
式［II］： ▲数式、化学式、表等があります▼［II］ （式中、Ｒ′はＨ、ｐ−ＣＮ、ｍ−ＣＮ、ｏ−ＣＮ、ｐ
−ＮＯ＿２、ｍ−ＮＯ＿２、ｏ−ＮＯ＿２、ｐ−ＣＨ＿
２Ｒｆまたはｍ−ＣＨ＿２Ｒｆ基を表わし、 Ｒｆは▲数式、化学式、表等があります▼基を表わす。 ） で表わされるペルフルオロヘキシルメチルベンゼン誘導
体の製造法。 ２、反応温度が室温〜約５０℃である第１項記載の方法
。[Claims] 1. Perfluoro-2-methylpent-2-ene and general formula [I]: ▲ Numerical formulas, chemical formulas, tables, etc. ▼ [I] (In the formula, R is H, p-CN, m -CN, o-CN, p-
NO_2, m-NO_2, o-NO_2, p-CH_2
General formula [II] characterized by reacting a benzyl bromide derivative represented by (representing Br or m-CH_2Br) in a dimethylformamide solvent in the presence of potassium fluoride supported on calcium fluoride: ▲Formula , chemical formulas, tables, etc. ▼ [II] (In the formula, R' is H, p-CN, m-CN, o-CN, p
-NO_2, m-NO_2, o-NO_2, p-CH_
Represents 2Rf or m-CH_2Rf group, Rf represents ▲group, which has numerical formula, chemical formula, table, etc. ) A method for producing a perfluorohexylmethylbenzene derivative represented by 2. The method according to item 1, wherein the reaction temperature is from room temperature to about 50°C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61254172A JPH0729958B2 (en) | 1986-10-24 | 1986-10-24 | Process for producing perfluorohexylmethylbenzene derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61254172A JPH0729958B2 (en) | 1986-10-24 | 1986-10-24 | Process for producing perfluorohexylmethylbenzene derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63107945A true JPS63107945A (en) | 1988-05-12 |
| JPH0729958B2 JPH0729958B2 (en) | 1995-04-05 |
Family
ID=17261232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61254172A Expired - Fee Related JPH0729958B2 (en) | 1986-10-24 | 1986-10-24 | Process for producing perfluorohexylmethylbenzene derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0729958B2 (en) |
-
1986
- 1986-10-24 JP JP61254172A patent/JPH0729958B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0729958B2 (en) | 1995-04-05 |
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