JPH05379B2 - - Google Patents
Info
- Publication number
- JPH05379B2 JPH05379B2 JP19532687A JP19532687A JPH05379B2 JP H05379 B2 JPH05379 B2 JP H05379B2 JP 19532687 A JP19532687 A JP 19532687A JP 19532687 A JP19532687 A JP 19532687A JP H05379 B2 JPH05379 B2 JP H05379B2
- Authority
- JP
- Japan
- Prior art keywords
- benzyltrimethylammonium
- group
- chlorobromate
- aromatic
- phenol
- 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
- KYSOGGYOHFQJCV-UHFFFAOYSA-N ClBr(=O)=O.C[N+](C)(C)CC1=CC=CC=C1 Chemical compound ClBr(=O)=O.C[N+](C)(C)CC1=CC=CC=C1 KYSOGGYOHFQJCV-UHFFFAOYSA-N 0.000 claims description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 9
- 150000004982 aromatic amines Chemical class 0.000 claims description 7
- 150000008378 aryl ethers Chemical class 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 5
- 150000002989 phenols Chemical class 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000031709 bromination Effects 0.000 description 7
- 238000005893 bromination reaction Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229910020314 ClBr Inorganic materials 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- -1 isobutoxyl group Chemical group 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
［発明の目的］
（産業上の利用分野）
本発明は、ベンジルトリメチルアンモニウムク
ロロブロメート（１−）及びそれを用いたフエノ
ール等のブロモ化法に関する。
［発明の構成］
（問題点を解決するための手段及び作用）
本発明は、ベンジルトリメチルアンモニウムク
ロロブロメート（１−）及びそれを用いたフエノ
ール及びその誘導体、芳香族アミン又は芳香族エ
ーテルのブロモ化法に関する。
本発明のベンジルトリメチルアンモニウムクロ
ロブロメート（１−）は、例えば、ベンジルトリ
メチルアンモニウムクロリドと等モル量の臭素の
ジクロロメタン溶液を室温で反応させることによ
り得ることができる。
次に、本発明のベンジルトリメチルアンモニウ
ムクロロブロメート（１−）を用いたフエノール
等のブロモ化法を説明する。まず、ベンジルトリ
メチルアンモニウムクロロブロメート（１−）と
フエノール及びその誘導体、芳香族アミン又は芳
香族エーテルを適当な溶媒中で、必要に応じて塩
基の存在下、室温で数分間迅速に反応させる。本
発明のベンジルトリメチルアンモニウムクロロブ
ロメート（１−）の基質に対する使用量は、理論
量あで充分である。その後、溶媒相に溶解してい
る目的物を分離し、生成することによりフエノー
ル及びその誘導体等のブロモ化物を容易に得るこ
とができる。かかるブロモ化法のうちフエノール
及びその誘導体のブロモ化の反応式を次に示す。
本発明のブロモ化法を適用できるフエノール及
びその誘導体、芳香族アミン又は芳香族エーテル
としては、芳香環の少なくとも一つの位置が非置
換のものであれば特に制限はない。かかる、各芳
香族化合物の芳香環の置換基としては、例えば、
メチル基、エチル基、プロピル基、イソプロピル
基、ブチル基、イソブチル基、sec−ブチル基、
tert−ブチル基、ペンチル基、ヘキシル基等のア
ルキル基；シクロヘキシル基等のシクロアルキル
基；メトキシ基、エトキシ基、プロポキシ基、イ
ソプロポキシ基、ブトキシ基、イソブトキシル
基、sec−ブトキシ基、tert−ブトキシ基等のア
ルコキシ基；ニトロ基；カルボキシ基；弗素原
子、塩素原子、臭素原子等のハロゲン原子などが
挙げられる。
本発明で用いる溶媒は、特に制限されるもので
はなく、ベンジルトリメチルアンモニウムクロロ
ブロメート（１−）を溶解することができるもの
であれば如何なるものであつてもよい。特に、ハ
ロゲン化アルキル溶媒、例えば、塩化メチレン、
クロロホルム、トリクレン、ジクロロエチレン等
は非常に高い溶解性を有し、反応溶媒として最適
である。また、この溶媒中に低級アルコール、例
えば、メタノール、エタノール、プロピルアルコ
ール、イソプロピルアルコール等を混入させると
ベンジルトリメチルアンモニウムクロロブロメー
ト（１−）の反応性が著しく高まる。特にメタノ
ールはその効果が著しい。ハロゲン化アルキル溶
媒とアルコールの混合比は特に制限されないが、
通常１：５〜10：１、好ましくは１：１〜５：１
である。
また、塩基は、ブロモ化後、副生する臭化水素
を補集する目的で使用するものであり、わずかの
溶解性があればよく、その意味においては炭酸カ
ルシウム、炭酸水素カルシウム、炭酸ナトリウ
ム、炭酸水素ナトリウム、炭酸カリウム、炭酸水
素カリウム等のアルカリ金属又はアルカリ土類金
属の炭酸塩又は炭酸水素塩が有効である。かかる
塩基の使用量は、ベンジルトリメチルアンモニウ
ムクロロブロメート（１−）と当量であれば充分
であるが、過剰であつても反応に悪影響を与える
ことはない。
（実施例）
以下、実施例を挙げて本発明をさらに詳しく説
明する。
実施例 １
臭素（15.98g，0.1mol）のジクロロメタン
（100ml）溶液に、ベンジルトリメチルアンモニウ
ムクロリド（18.57g，0.1mol）の水（100ml）溶
液を、室温下、攪拌しながら滴下した。30分間攪
拌したのち、ジクロロメタン相を分離し、これを
硫酸マグネシウムで乾燥した。次いで、減圧下で
ジクロロメタンを蒸発させて得た残渣を10倍量
（重量比）のジクロロメタンエーテルを用いて再
結晶させて、安定なオレンジ色の結晶のベンジル
トリメチルアンモニウムクロロブロメート（１
−）を得た。
収量は24.50g（収率71％）であり、その融点は
101−102℃であつた。また、その元素組成を下記
に示す。
実験値（％）：Ｃ，34.88；Ｈ，4.63；Ｎ，
4.01；ClBr2，56.31
計算値（％）：Ｃ，34.76；Ｈ，4.67；Ｎ，
4.05；ClBr2，56.51
実施例 ２
２，４，６−トリブロムフエノールの製造
フエノール（0.50g，5.51mmol）のジクロロメ
タン50mlとメタノール20mlの混合溶媒に、室温
下、ベンジルトリメチルアンモニウムクロロブロ
メート（１−）（5.69g，16.47mmol）及び炭酸カ
ルシウム粉末2gを添加した。この混合物を生じ
たオレンジ色が消えるまで20分間攪拌した。その
後、炭酸カルシウムをろ別したのち、ろ液を濃縮
して得た残渣に水20mlを加えた。次いで、この残
渣と水の混合物に対してエーテル40mlを用いて合
計４回の抽出処理を行つた。その後、得られたエ
ーテル相を硫酸マグネシウムで乾燥した。次い
で、減圧下でエーテルを蒸発除去して得た残渣
を、３倍量（重量比）のメタノールと水の混合溶
媒を用いて再結晶させて無色結晶の２，４，６−
トリブロムフエノールを得た。
収量は1.64g（収率93％）であり、その融点は91
−92℃であつた。
実施例 ３
第１表に示す各原料を用い、実施例２と同様に
してブロモ化を行い第１表に示す各生成物を得
た。結果を第１表に示す。なお、表中、Meはメ
チル基を表し、Etはエチル基を表し、Buはブチ
ル基を表す。また、モル比は、ベンジルトリメチ
ルアンモニウムクロロブロメート（１−）と原料
のモル比である。
[Object of the Invention] (Industrial Application Field) The present invention relates to benzyltrimethylammonium chlorobromate (1-) and a method for brominating phenol, etc. using the same. [Structure of the Invention] (Means and Effects for Solving the Problems) The present invention provides benzyltrimethylammonium chlorobromate (1-) and the bromolysis of phenol and its derivatives, aromatic amines or aromatic ethers using the same. Concerning the law. Benzyltrimethylammonium chlorobromate (1-) of the present invention can be obtained, for example, by reacting benzyltrimethylammonium chloride with a dichloromethane solution of an equimolar amount of bromine at room temperature. Next, a method for brominating phenol etc. using benzyltrimethylammonium chlorobromate (1-) of the present invention will be explained. First, benzyltrimethylammonium chlorobromate (1-) and phenol and its derivatives, aromatic amines or aromatic ethers are rapidly reacted for several minutes at room temperature in an appropriate solvent, optionally in the presence of a base. The amount of benzyltrimethylammonium chlorobromate (1-) used in the present invention relative to the substrate is sufficient to be the theoretical amount. Thereafter, by separating and producing the target substance dissolved in the solvent phase, brominated products such as phenol and its derivatives can be easily obtained. Among such bromination methods, the reaction formula for bromination of phenol and its derivatives is shown below. The phenol and its derivatives, aromatic amines or aromatic ethers to which the bromination method of the present invention can be applied are not particularly limited as long as at least one position of the aromatic ring is unsubstituted. Such substituents on the aromatic ring of each aromatic compound include, for example,
Methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group,
Alkyl groups such as tert-butyl group, pentyl group, hexyl group; cycloalkyl groups such as cyclohexyl group; methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxyl group, sec-butoxy group, tert-butoxy Examples include alkoxy groups such as groups; nitro groups; carboxy groups; halogen atoms such as fluorine atoms, chlorine atoms, and bromine atoms. The solvent used in the present invention is not particularly limited, and any solvent may be used as long as it can dissolve benzyltrimethylammonium chlorobromate (1-). In particular, halogenated alkyl solvents, such as methylene chloride,
Chloroform, trichlene, dichloroethylene, etc. have extremely high solubility and are optimal as reaction solvents. Furthermore, when a lower alcohol such as methanol, ethanol, propyl alcohol, isopropyl alcohol, etc. is mixed into this solvent, the reactivity of benzyltrimethylammonium chlorobromate (1-) increases significantly. In particular, methanol has a remarkable effect. The mixing ratio of the halogenated alkyl solvent and alcohol is not particularly limited, but
Usually 1:5 to 10:1, preferably 1:1 to 5:1
It is. In addition, the base is used for the purpose of collecting hydrogen bromide produced as a by-product after bromination, and only needs to have slight solubility. Carbonates or hydrogen carbonates of alkali metals or alkaline earth metals such as sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, etc. are effective. The amount of such base used is sufficient if it is equivalent to benzyltrimethylammonium chlorobromate (1-), but even if it is in excess, it will not adversely affect the reaction. (Example) Hereinafter, the present invention will be explained in more detail by giving examples. Example 1 A solution of benzyltrimethylammonium chloride (18.57 g, 0.1 mol) in water (100 ml) was added dropwise to a solution of bromine (15.98 g, 0.1 mol) in dichloromethane (100 ml) at room temperature with stirring. After stirring for 30 minutes, the dichloromethane phase was separated and dried over magnesium sulfate. Next, the residue obtained by evaporating dichloromethane under reduced pressure was recrystallized using 10 times the amount (by weight) of dichloromethane ether to obtain stable orange crystals of benzyltrimethylammonium chlorobromate (1
-) was obtained. The yield is 24.50g (yield 71%) and its melting point is
It was 101-102℃. Moreover, its elemental composition is shown below. Experimental value (%): C, 34.88; H, 4.63; N,
4.01; ClBr 2 , 56.31 Calculated value (%): C, 34.76; H, 4.67; N,
4.05; ClBr 2 , 56.51 Example 2 Production of 2,4,6-tribromophenol Benzyltrimethylammonium chlorobromate (1 ) (5.69 g, 16.47 mmol) and 2 g of calcium carbonate powder were added. The mixture was stirred for 20 minutes until the resulting orange color disappeared. Then, after filtering off calcium carbonate, the filtrate was concentrated and 20 ml of water was added to the resulting residue. Next, the mixture of this residue and water was extracted a total of 4 times using 40 ml of ether. The resulting ether phase was then dried over magnesium sulfate. Next, the residue obtained by removing the ether by evaporation under reduced pressure was recrystallized using a mixed solvent of methanol and water of 3 times the amount (weight ratio) to obtain colorless crystals of 2,4,6-
Tribromophenol was obtained. The yield is 1.64g (93% yield) and its melting point is 91
It was -92℃. Example 3 Using each raw material shown in Table 1, bromination was carried out in the same manner as in Example 2 to obtain each product shown in Table 1. The results are shown in Table 1. In addition, in the table, Me represents a methyl group, Et represents an ethyl group, and Bu represents a butyl group. Further, the molar ratio is the molar ratio between benzyltrimethylammonium chlorobromate (1-) and the raw material.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】
＊ 炭酸カルシウムを使用した例である。
実施例 ４
第２表に示す芳香族アミンを用い、実施例２と
同様にしてブロモ化を行い第２表に示す各生成物
を得た。結果を第２表に示す。[Table] *This is an example using calcium carbonate.
Example 4 Using the aromatic amines shown in Table 2, bromination was carried out in the same manner as in Example 2 to obtain each product shown in Table 2. The results are shown in Table 2.
【表】【table】
【表】【table】
【表】
実施例 ５
第３表に示す芳香族エーテルを用い、実施例２
と同様にしてブロモ化を行い第３表に示す各生成
物を得た。結果を第３表に示す。[Table] Example 5 Using the aromatic ether shown in Table 3, Example 2
Bromination was carried out in the same manner as above to obtain each product shown in Table 3. The results are shown in Table 3.
【表】【table】
【表】
［発明の効果］
本発明のベンジルトリメチルアンモニウムクロ
ロブロメート（１−）を用いることにより、高収
率で容易にフエノール及びその誘導体、芳香族ア
ミン又は芳香族エーテルのブロモ化物を得ること
ができる。[Table] [Effects of the invention] By using benzyltrimethylammonium chlorobromate (1-) of the present invention, brominated products of phenol and its derivatives, aromatic amines or aromatic ethers can be easily obtained in high yield. I can do it.
Claims (1)
メート（１−）。 ２ フエノール及びその誘導体、芳香族アミン又
は芳香族エーテルをベンジルトリメチルアンモニ
ウムクロロブロメート（１−）で処理することを
特徴とするフエノール及びその誘導体、芳香族ア
ミン又は芳香族エーテルのブロモ化法。[Claims] 1 Benzyltrimethylammonium chlorobromate (1-). 2. A method for brominating phenol and its derivatives, aromatic amines or aromatic ethers, which comprises treating phenols and their derivatives, aromatic amines or aromatic ethers with benzyltrimethylammonium chlorobromate (1-).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19532687A JPS6440448A (en) | 1987-08-06 | 1987-08-06 | Benzyltrimethylammonium chlorobromate(1-) and bromination using said chlorobromate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19532687A JPS6440448A (en) | 1987-08-06 | 1987-08-06 | Benzyltrimethylammonium chlorobromate(1-) and bromination using said chlorobromate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6440448A JPS6440448A (en) | 1989-02-10 |
| JPH05379B2 true JPH05379B2 (en) | 1993-01-05 |
Family
ID=16339305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19532687A Granted JPS6440448A (en) | 1987-08-06 | 1987-08-06 | Benzyltrimethylammonium chlorobromate(1-) and bromination using said chlorobromate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6440448A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4015592A1 (en) * | 1990-05-15 | 1991-11-21 | Boehringer Mannheim Gmbh | METHOD FOR DETERMINING AN ION WITH INCREASED SENSITIVITY, USE THEREOF OF SUITABLE SUBSTANCES AND CORRESPONDING MEANS |
-
1987
- 1987-08-06 JP JP19532687A patent/JPS6440448A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6440448A (en) | 1989-02-10 |
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