CN100522932C - Method for preparing 2-bromomethyl-2-phenyl-4-(4-chlorophenyl)-butyronitrile - Google Patents
Method for preparing 2-bromomethyl-2-phenyl-4-(4-chlorophenyl)-butyronitrile Download PDFInfo
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- CN100522932C CN100522932C CNB2007101311455A CN200710131145A CN100522932C CN 100522932 C CN100522932 C CN 100522932C CN B2007101311455 A CNB2007101311455 A CN B2007101311455A CN 200710131145 A CN200710131145 A CN 200710131145A CN 100522932 C CN100522932 C CN 100522932C
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Abstract
The invention relates to a 2-bromomethyl-2-phenyl-4-(4-chlorophenyl)-butyronitrile preparation method, which takes 2-phenyl-4-(4-chlorophenyl)-butyronitrile and dibromomethane as raw materials and sodium hydroxide as an acid binding agent, and the invention is characterized in that the reaction is processed with the existing of catalyst until the 2-phenyl-4-(4-chlorophenyl)-butyronitrile is completely converted into 2-bromomethyl-2-phenyl-4-(4-chlorophenyl)-butyronitrile, and when the reaction finishes, the reactant obtained from the reaction is settled stationarily and layered, after the alkali liquid layer is separated, the acquired liquid is 2-bromomethyl-2- phenyl-4-(4-chlorophenyl)-butyronitrile which can be used as the intermediate of nitrile benzenezole which is an agricultural fungicide. Application of solvent of dimethyl sulfoxide and extraction solvent of 1, 2-dichloroethane are avoided in the method, thereby reducing the cost, decreasing pollution and discharge of sewage and shortening the process, and the preparation method is environmental friendly, with prominent economic benefit.
Description
Technical field
The present invention relates to the preparation method of a kind of 2-brooethyl-2-phenyl-4-(4-chloro-phenyl-)-butyronitrile, more specifically say, relate to a kind of preparation method of intermediate 2-brooethyl-2-phenyl-4-(4-chloro-phenyl-)-butyronitrile of disinfectant use in agriculture RH-7592.
Background technology
RH-7592 is that its chemical name is 4-(4-chloro-phenyl-)-2-phenyl-2-(1H-1,2,4-triazol-1-yl methyl) butyronitrile by the triazole bactericidal agent of Rohm and Hass company (now being Dow Agro Seiences company) exploitation, and chemical structural formula is:
RH-7592 is a sterol demethylation inhibitor, is interior absorption conduction type sterilant.Can suppress the elongation of pathogenic bacteria mycelia, stop spore to be invaded and make fabric texture, the existing prophylactic effect of disease is had therapeutic action again.Being mainly used in the disease of control cereal crop, paddy rice, beet, grape, banana, fruit tree crops such as (as peach, apples), is a kind of sterilant of excellent property.Intermediate 2-brooethyl-2-phenyl-4-(4-the chloro-phenyl-)-butyronitrile of RH-7592 is to adopt following method preparation at present, be starting raw material promptly with 2-phenyl-4-(4-chloro-phenyl-)-butyronitrile and methylene bromide, with the dimethyl sulfoxide (DMSO) is solvent, sodium hydroxide with 50% is acid binding agent, react at proper temperature with in the time, then with after the products therefrom washing, again with toluene or 1, the extraction of 2-ethylene dichloride removes solvent through underpressure distillation and makes 2-brooethyl-2-phenyl-4-(4-chloro-phenyl-)-butyronitrile.The disadvantage of this method is: solvent-oil ratio is big, and not only cost height, and solvent all has harm to human body and environment, and in addition, production process is also discharged large amount of sewage, makes the sewage disposal expense increase.Therefore, influence the suitability for industrialized production of RH-7592, and then influenced applying of RH-7592.
Summary of the invention
The objective of the invention is to, provide a kind of and reduce cost, reduce pollution, shorten the preparation method of 2-brooethyl-2-phenyl-4-(4-the chloro-phenyl-)-butyronitrile of operation.
The technical scheme that realizes the object of the invention is: the preparation method of a kind of 2-brooethyl-2-phenyl-4-(4-chloro-phenyl-)-butyronitrile, it is to be starting raw material with 2-phenyl-4-(4-chloro-phenyl-)-butyronitrile and methylene bromide, sodium hydroxide is acid binding agent, be characterized in, in the presence of catalyzer, react, till 2-phenyl-4-(4-chloro-phenyl-)-butyronitrile is converted into 2-brooethyl-2-phenyl-4-(4-chloro-phenyl-)-butyronitrile fully, after reaction finishes, standing demix, after separating the alkali lye layer, gained liquid is 2-brooethyl-2-phenyl-4-(4-chloro-phenyl-)-butyronitrile.
Among the above-mentioned preparation method, described catalyzer is a quaternary ammonium salt.
Among the above-mentioned preparation method, the quaternary ammonium salt that is used as catalyzer is one or more in trimethyl benzyl ammonia chloride, trimethyl benzyl p-chlorobenzyl ammonium chloride, triethyl benzyl ammonia chloride, triethyl p-chlorobenzyl ammonium chloride, the Tetrabutyl amonium bromide.
Among the above-mentioned preparation method, described sodium hydroxide is 50% or 30% the aqueous solution.
Among the above-mentioned preparation method, describedly react in the presence of catalyzer, the temperature of its reaction is 20～100 ℃.
Among the above-mentioned preparation method, describedly react in the presence of catalyzer, the feed ratio of its 2-phenyl-4-(4-chloro-phenyl-)-butyronitrile, methylene bromide, sodium hydroxide is 1:2～4:2～4 with the molar ratio computing.
Among the above-mentioned preparation method, described catalyzer reacts under existing, and the feed ratio of its 2-phenyl-4-(4-chloro-phenyl-)-butyronitrile, methylene bromide, sodium hydroxide is preferably 1:2.25～2.50:3.6 with molar ratio computing.
Among the above-mentioned preparation method, describedly in the presence of catalyzer, react, its catalyst levels be by weight 2-phenyl-4-(4-chloro-phenyl-)-butyronitrile charging capacity 3%～9%.
Technique effect of the present invention: preparation method of the present invention is that the method for solvent is compared with adopting dimethyl sulfoxide (DMSO), because the reaction of 2-phenyl-4-(4-chloro-phenyl-)-butyronitrile, methylene bromide, sodium hydroxide is carried out in the presence of catalyzer, therefore, has following beneficial effect: 1. can not use solvent dimethyl sulfoxide (DMSO) and extraction solvent 1, the 2-ethylene dichloride makes expense of raw materials reduce.Need the dimethyl sulfoxide (DMSO) of 906.0 kilograms of consumption to calculate by 2-brooethyl per ton-2-phenyl-4-(4-chloro-phenyl-)-butyronitrile (100%), present dimethyl sulfoxide (DMSO) market price per ton is 1.6 ten thousand yuan, that is to say that without dimethyl sulfoxide (DMSO) 1 ton of 2-brooethyl-2-phenyl-4-of every production (4-chloro-phenyl-)-butyronitrile can be saved 1.4496 ten thousand yuan; Method of the present invention need not to use solvent extraction, and former arts demand is with 1, the extraction of 2-ethylene dichloride, consume 1 by 2-brooethyl per ton-2-phenyl-4-(4-chloro-phenyl-)-butyronitrile, 1.1617 tons of calculating of 2-ethylene dichloride, present per ton 1,2-ethylene dichloride market price is 0.8 ten thousand yuan, that is to say that 1 ton of 2-brooethyl-2-phenyl-4-of every production (4-chloro-phenyl-)-butyronitrile can save extraction solvent and take 0.9294 ten thousand yuan, but more than two conservations take 2.3790 ten thousand yuan, though the present invention has used catalyzer, but, catalyzer do not have only a small amount of loss because not participating in reaction substantially, to use triethyl benzyl ammonia chloride to be example as catalyzer, 1 ton of 2-brooethyl-2-phenyl-4-of every production (4-chloro-phenyl-)-butyronitrile, the loss of catalyzer is 51.12 kilograms, and 20,000 yuan of catalyzer per ton (self-control), the catalyst costs of institute's loss is 0.1020 ten thousand yuan, therefore, the wear and tear expense of deduction catalyzer, by the inventive method produce 1 ton of 2-brooethyl-2-phenyl-4-(4-chloro-phenyl-) but-butyronitrile still conservation take 2.2768 ten thousand yuan, economic benefit is fairly obvious; 2. do not use solvent dimethyl sulfoxide (DMSO) and extraction solvent 1, the 2-ethylene dichloride, expense not only economizes in raw materials, also the sewage quantity with former method is reduced to 1 ton from 2-brooethyl per ton-2-phenyl-4-(4-chloro-phenyl-)-13 tons of sewage of butyronitrile generation, saved the wastewater treatment expense, also reduced to the pollution of environment and to operator's harm, therefore, preparation method of the present invention belongs to environmentally friendly preparation method, meets very much the environmental requirement of present country; 3. owing to used catalyzer when reaction, saved extraction process, made production process and equipment reduce, production efficiency improves.Therefore, preparation method of the present invention is more conducive to the suitability for industrialized production of RH-7592.
Embodiment
Below in conjunction with embodiment the present invention is further described in detail, but is not limited to this.
Unless otherwise indicated raw materials used among the embodiment, be commercially available industrial goods.
The main raw material specification:
2-phenyl-4-(4-chloro-phenyl-)-butyronitrile purity is 93.4%;
Concentration of sodium hydroxide solution is 50% or 30%;
Methylene bromide purity is 100%;
The related chemical equation of the preparation method of 2-brooethyl of the present invention-2-phenyl-4-(4-chloro-phenyl-)-butyronitrile is as follows:
Embodiment 1 preparation 2-brooethyl-2-phenyl-4-(4-chloro-phenyl-)-butyronitrile
With the quaternary ammonium salt triethyl benzyl ammonia chloride as catalyzer;
The feed ratio of 2-phenyl-4-(4-chloro-phenyl-) butyronitrile, methylene bromide, sodium hydroxide is counted 0.03:0.12:0.108=1:4.0:3.6 by mole
Agitator is being housed, condenser, thermometer, in three mouthfuls of reaction flasks of the 250ml of dropping funnel, 2-phenyl-4-(4-the chloro-phenyl-)-butyronitrile (being equivalent to 0.03mol) that adds 8.21g93.4%, the methylene bromide of 20.86g100% (being equivalent to 0.12mol), and the triethyl benzyl ammonia chloride of adding 0.25g, open stirring, control reaction temperature is between 40～60 ℃, drip the aqueous sodium hydroxide solution (being equivalent to 0.108mol) of 14.4g30%, in 2 hours, drip off and insulation reaction under this temperature, use the gas-chromatography trace analysis between the reaction period, till 2-phenyl-4-(4-chloro-phenyl-)-butyronitrile is converted into 2-brooethyl-2 phenyl-4 (4-chloro-phenyl-)-butyronitrile fully, after reaction finishes, standing demix, after separating the alkali lye layer, gained 10.89g liquid is 2-brooethyl-2 phenyl-4 (4-chloro-phenyl-)-butyronitrile, and the gas-chromatography normalization method is analyzed, content 82.0%, yield 85.6%.
Embodiment 2 preparation 2-brooethyl-2-phenyl-4-(4-chloro-phenyl-)-butyronitrile
With triethyl p-chlorobenzyl ammonium chloride and Tetrabutyl amonium bromide as catalyzer;
The feed ratio of 2-phenyl-4-(4-chloro-phenyl-)-butyronitrile, methylene bromide, sodium hydroxide is counted 0.06:0.12:0.216=1:2.0:3.6 by mole
Agitator is being housed, condenser, thermometer, in three mouthfuls of reaction flasks of the 250ml of dropping funnel, 2-phenyl-4-(4-the chloro-phenyl-)-butyronitrile (being equivalent to 0.06mol) that adds 16.41g93.4%, the methylene bromide of 20.86g100% (being equivalent to 0.12mol), and adding 0.6g triethyl p-chlorobenzyl ammonium chloride and 0.7g Tetrabutyl amonium bromide, open stirring, control reaction temperature is between 40～60 ℃, drip 17.28g50% aqueous sodium hydroxide solution (being equivalent to 0.216mol), in 2 hours, drip off and insulation reaction under this temperature, use the gas-chromatography trace analysis between the reaction period, till 2-phenyl-4-(4-chloro-phenyl-) butyronitrile is converted into 2-brooethyl-2 phenyl-4 (4-chloro-phenyl-)-butyronitrile fully, after reaction finishes, standing demix, after separating the alkali lye layer, gained 23.1g liquid is 2-brooethyl-2 phenyl-4 (4-chloro-phenyl-)-butyronitrile, and the gas-chromatography normalization method is analyzed, content 76.5%, yield 84.7%.
Embodiment 3 preparation 2-brooethyl-2-phenyl-4-(4-chloro-phenyl-)-butyronitrile
With Tetrabutyl amonium bromide as catalyzer;
The feed ratio of 2-phenyl-4-(4-chloro-phenyl-)-butyronitrile, methylene bromide, sodium hydroxide is counted 0.06:0.15:0.216=1:2.5:3.6 by mole
Agitator is being housed, condenser, thermometer, in three mouthfuls of reaction flasks of the 250ml of dropping funnel, 2-phenyl-4-(4-the chloro-phenyl-)-butyronitrile (being equivalent to 0.06mol) that adds 16.41g93.4%, 26.07g100% methylene bromide (being equivalent to 0.15mol) also adds the 1.0g Tetrabutyl amonium bromide, open stirring, control reaction temperature is between 40～60 ℃, drip 17.28g50% aqueous sodium hydroxide solution (being equivalent to 0.216mol), in 2 hours, drip off, and under this temperature insulation reaction, use the gas-chromatography trace analysis between the reaction period, till 2-phenyl-4-(4-chloro-phenyl-)-butyronitrile is converted into 2-brooethyl-2 phenyl-4 (4-chloro-phenyl-)-butyronitrile fully, after reaction finishes, standing demix, after separating the alkali lye layer, gained 23.0g liquid is 2-brooethyl-2 phenyl-4 (4-chloro-phenyl-)-butyronitrile, and the gas-chromatography normalization method is analyzed, content 86.6%, yield 95.5%.
Embodiment 4 preparation RH-7592
In three mouthfuls of reaction flasks of the 250ml that agitator, reflux condensing tube, thermometer, dropping funnel are housed, the 1H-1 that adds 2.59g96% successively, 2, the potassium hydroxide (being equivalent to 0.036mol) of 4-triazole (being equivalent to 0.036mol) and 2.46g82%, the 40ml dimethyl sulfoxide (DMSO) stirs.Be heated to 90 ℃, treat that potassium hydroxide all dissolves the back and adds 40ml toluene, back flow reaction 4 hours.Being warming up to 165 ℃ of water with toluene and reaction generation gradually steams.When question response liquid was cooled to 130 ℃, 2-brooethyl-2-phenyl-(4-chloro-phenyl-)-butyronitrile (being equivalent to 0.03mol) that the 13.1g embodiment 1,2 or 3 that dropping is diluted with the 10ml dimethyl sulfoxide (DMSO) makes added in the 15min.Continued insulation reaction 4 hours, reaction finishes.Reaction solution is cooled to room temperature, adds 50ml water and 40ml ethyl acetate then, transfers pH to neutral, and standing demix, water layer are used ethyl acetate extraction 2 times (30ml/ time) again.Organic layer merges with the 50ml washing once again, gets crude product behind the drying precipitation.Crude product is dissolved in ethanol, the dry hydrogen chloride gas of throughput, the adularescent solid is separated out.After treating that salify fully, cooling is left standstill a few hours, takes advantage of cold filtration then, and 9.14g (by 100%) weighs after the solid oven dry that leaches.The RH-7592 yield is 81.6% (amount of pressing the hydrochloride of RH-7592 converts).
The RH-7592 that makes is detected:
Through mass spectrum and proton nmr spectra checking, determine that the product that makes is a RH-7592;
Fusing point: 126.4 ℃～127.3 ℃ (124～126 ℃ of literature values);
Molecular weight: adopt direct injection, ESI ion source positive ion mode, molecular ion peak are M/Z[M+1] 337.34 promptly to survey the RH-7592 molecular weight be 336.34 (literature value is 336.8);
The gas-chromatography appearance time is consistent with standard substance.
Above-mentioned detected result proves that 2-brooethyl-2-phenyl-(4-the chloro-phenyl-)-butyronitrile that makes with the inventive method can be used as the intermediate of RH-7592 and can obtain qualified RH-7592.
Claims (8)
1, the preparation method of a kind of 2-brooethyl-2-phenyl-4-(4-chloro-phenyl-)-butyronitrile, it is to be starting raw material with 2-phenyl-4-(4-chloro-phenyl-)-butyronitrile and methylene bromide, sodium hydroxide is acid binding agent, it is characterized in that, in the presence of catalyzer, react, till 2-phenyl-4-(4-chloro-phenyl-)-butyronitrile is converted into 2-brooethyl-2-phenyl-4-(4-chloro-phenyl-)-butyronitrile fully, after reaction finishes, standing demix, after separating the alkali lye layer, gained liquid is 2-brooethyl-2-phenyl-4-(4-chloro-phenyl-)-butyronitrile.
2, preparation method according to claim 1 is characterized in that, described catalyzer is a quaternary ammonium salt.
3, preparation method according to claim 2, it is characterized in that the quaternary ammonium salt that is used as catalyzer is one or more in trimethyl benzyl ammonia chloride, trimethyl benzyl p-chlorobenzyl ammonium chloride, triethyl benzyl ammonia chloride, triethyl p-chlorobenzyl ammonium chloride, the Tetrabutyl amonium bromide.
4, preparation method according to claim 1 is characterized in that, described sodium hydroxide is 50% or 30% the aqueous solution.
5, preparation method according to claim 1 is characterized in that, describedly reacts in the presence of catalyzer, and the temperature of its reaction is 20～100 ℃.
6, preparation method according to claim 1 is characterized in that, describedly reacts in the presence of catalyzer, and the feed ratio of its 2-phenyl-4-(4-chloro-phenyl-)-butyronitrile, methylene bromide, sodium hydroxide is 1:2～4:2～4 with the molar ratio computing.
7, preparation method according to claim 6 is characterized in that, described catalyzer reacts under existing, the feed ratio of its 2-phenyl-4-(4-chloro-phenyl-)-butyronitrile, methylene bromide, sodium hydroxide, with molar ratio computing be preferably 1: 2.25～2.50: 3.6.
8, preparation method according to claim 1 is characterized in that, describedly in the presence of catalyzer, react, its catalyst levels be by weight 2-phenyl-4-(4-chloro-phenyl-)-butyronitrile charging capacity 3%～9%.
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| CN110684112A (en) * | 2019-10-15 | 2020-01-14 | 北京勤邦生物技术有限公司 | Preparation and application of fenbuconazole monoclonal antibody |
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Denomination of invention: Preparation of 2-bromomethyl-2-phenyl-4 - (4-chlorophenyl) - Nitrile Effective date of registration: 20191012 Granted publication date: 20090805 Pledgee: Jiangsu Jiangnan Rural Commercial Bank Limited by Share Ltd Pledgor: JIANGSU FENGDENG CROP SCIENCE CO., LTD. Registration number: Y2019320010015 |
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