CN116396142A - 一种3,4,5-三氟溴苯的生产工艺 - Google Patents
一种3,4,5-三氟溴苯的生产工艺 Download PDFInfo
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- 238000000746 purification Methods 0.000 description 5
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- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0244—Nitrogen containing compounds with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine
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Abstract
本发明涉及有机化学技术领域,尤其是涉及一种3,4,5‑三氟溴苯的生产工艺,本发明以4‑溴‑2,6‑二氟苯酚为原料,在催化剂Cat的作用下制备得到3,4,5‑三氟溴苯,本发明的生产工艺简单,仅需一步反应,催化剂用量低,反应收率高,纯度高,且具有无需使用溴素和磷酸盐等环境不友好的试剂,副产物少,分离纯化简单等优点。
Description
技术领域
本发明涉及有机化学技术领域,尤其是涉及一种3,4,5-三氟溴苯的生产工艺。
背景技术
3,4,5-三氟溴苯分子式为C6H2BrF3,分子量为210.98,CAS登记号为138526-69-9。3,4,5-三氟溴苯进行格氏反应实现各种官能化,进一步合成各种多氟取代化合物,因而广泛用于液晶材料,医药及农药中间体等,其化学结构式如下:
目前国内3,4,5-三氟溴苯的生产工艺主要有以下几种:
中国专利文献CN103601613A公开一种3,4,5-三氟溴苯的生产工艺:2,3,4-三氟苯胺先经溴素溴化得到2,3,4-三氟-6-溴苯胺,再重氮化脱氨基得到3,4,5-三氟溴苯,反应方程式如下:
该工艺用到有强烈毒害作用和腐蚀性的溴素,重氮化脱氨基过程还需要使用次磷酸和铜催化剂,会产生含磷重金属废水,环保处置成本高,也不利于操作人员的职业健康保护。
中国专利文献CN108947763A公开一种3,4,5-三氟溴苯的生产工艺:以1,2,3-三氟苯为起始原料,先分散于有机溶剂重再与含有缓冲盐的溴化钠水溶液混合,滴加次氯酸钠水溶液,得到3,4,5-三氟溴苯粗品,熔融结晶即得3,4,5-三氟溴苯成品,化学反应方程式如下:
2020年,尹凯基对上述工艺进行优化,于《世界农药》2020年第42卷第4期第54-56页发表篇名为《3,4,5-三氟溴苯合成新工艺》的论文,该论文报道3,4,5-三氟溴苯可由1,2,3-三氯苯为起始原料,经氟化、溴化两步反应合成3,4,5-三氟溴苯,反应方程式如下:
该工艺只是改变了起始原料,反应本质无改变,仍然产生高磷废水,另外,该工艺产生的副产物氯化钾和氯化钠纯度较低,需作为废盐处置,故该工艺环保费用极高,市场竞争力不强,工业化可行性低。
综上所述,目前现有技术中公开的3,4,5-三氟溴苯的生产工艺,存在反应路线长、收率低、纯度低、使用大量环境不友好的原料(如:溴素)、会产生高磷废水以及易产生多种溴代副产物、产品不易纯化等问题。因此,亟需提供一种反应路线短、原料来源简单、环境友好、不产生高磷废水、副产物少、易纯化、收率高的3,4,5-三氟溴苯的生产工艺。
发明内容
本发明的目的在于提供一种提供一种反应路线短、原料来源简单、环境友好、不产生高磷废水、副产物少、易纯化、收率高的3,4,5-三氟溴苯的生产工艺,以解决现有技术中存在的反应路线长、收率低、纯度低、使用大量环境不友好的原料(如:溴素)、会产生高磷废水以及易产生多种溴代副产物、产品不易纯化的技术问题。
为解决上述技术问题,本发明提供了一种如下合成路线:
具体操作为:
1)将化合物1和催化剂Cat的甲苯溶液在室温下搅拌30分钟,随后加热升温至110℃,恒温搅拌反应30分钟,反应完毕后冷却至室温,过滤,浓缩,硅胶柱色谱纯化,得到化合物2。
进一步地,所述步骤1)中化合物1和催化剂Cat的摩尔比为1:1-5;更优选地摩尔比为1:1.5或者1:2或者1:3;
本发明的有益效果在于:
1)本发明的3,4,5-三氟溴苯的生产工艺简单,仅需一步反应,催化剂用量低,反应收率高,纯度高;
2)本发明的3,4,5-三氟溴苯的生产工艺,具有无需使用溴素和磷酸盐等环境不友好的试剂,副产物少,分离纯化简单等优点。
附图说明
1)图1为化合物8的1H NMR谱图。
具体实施方式
下面将结合实施例对本发明的技术方案进行清楚、完整地描述,显然,所描述的实施例是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例,都属于本发明保护的范围。
下面结合具体的实施方式对本发明做进一步的解释说明。
实施例1催化剂Cat化合物8的合成:
合成步骤:
1)向500mL圆底烧瓶中加入207.3g化合物3(1mol)、43.0g化合物4(0.5mol)、0.5mL甲酸和300mL甲醇溶液,室温下搅拌过夜,过滤,滤饼用甲醇洗涤(3*150mL),干燥,得到141.7g化合物5,收率61%。
2)取步骤1)制备的干燥的化合物5(46.5g,0.1mol)和多聚甲醛(3g,0.1mol)置于800mL乙酸乙酯溶液中,在70℃下缓慢滴加用10mL乙酸乙酯稀释的三甲基氯硅烷(TMSCl,12.7mL,0.1mol),45分钟内滴加完毕,滴加完毕后,70℃下继续反应2小时,随后,反应液冷却至10℃,过滤,滤饼用乙酸乙酯洗涤(3*150mL),真空干燥,得到33.4g化合物6,收率65%。1H NMR(400MHz,CDCl3,δ):9.68(s,1H),7.04(s,4H),3.95(s,6H),2.39-2.30(m,4H),2.15(s,6H),1.35(d,12H),1.26(d,12H)。
3)取步骤2)制备的化合物6(25.6g,0.05mol)和叔丁醇钾(6.7g,0.06mol)置于250mL干燥的圆底烧瓶中,并用氮气进行保护,然后加入100mL四氢呋喃,室温下,搅拌反应4小时,反应混合物冷却至-40℃,缓慢滴加1,1,1,2,2,2-六氯乙烷(14.2g,0.06mol),滴加完毕后,反应液升温至室温,继续搅拌24小时,反应液冷却至-40℃,过滤,滤饼用冷的四氢呋喃(-20℃,3*50mL)和甲苯(2*50mL)分别洗涤,随后用100mL二氯甲烷溶解滤饼,并用硅藻土过滤,再用二氯甲烷(3*50mL)洗涤,减压浓缩滤液,得到残余物,再真空干燥得到21.9g化合物7,收率,80%。1H NMR(400MHz,CDCl3,δ):7.03(s,4H),3.93(s,6H),2.55-2.31(m,4H),2.17(s,6H),1.48-1.46(d,,12H),1.31-1.30(d,12H)。
4)在空气中,向干燥的小瓶中加入化合物7(21.9g,0.04mol)和CsF(44.0g,0.29mol),充分摇匀上述混合物,得到65.9g化合物8,并向小瓶中注入氮气保存。
实施例2化合物2的制备
合成步骤:
取20.9化合物1(0.1mol)和104.9g实施例1制备的催化剂Cat化合物8(0.15mol)置于800mL甲苯溶液中,在室温下搅拌30分钟,随后加热升温至110℃,恒温搅拌反应30分钟,反应完毕后冷却至室温,过滤,浓缩,硅胶柱色谱纯化,洗脱剂为10%乙醚的正己烷溶液,得到15.0g化合物2(0.071mol),收率71%。
实施例3化合物2的制备
合成步骤:
取20.9化合物1(0.1mol)和139.9g实施例1制备的催化剂Cat化合物8(0.2mol)置于800mL甲苯溶液中,在室温下搅拌30分钟,随后加热升温至110℃,恒温搅拌反应30分钟,反应完毕后冷却至室温,过滤,浓缩,硅胶柱色谱纯化,洗脱剂为10%乙醚的正己烷溶液,得到16.9g化合物2(0.080mol),收率80%。
实施例4化合物2的制备
合成步骤:
取20.9化合物1(0.1mol)和209.8g实施例1制备的催化剂Cat化合物8(0.3mol)置于800mL甲苯溶液中,在室温下搅拌30分钟,随后加热升温至110℃,恒温搅拌反应30分钟,反应完毕后冷却至室温,过滤,浓缩,硅胶柱色谱纯化,洗脱剂为10%乙醚的正己烷溶液,得到18.1g化合物2(0.086mol),收率86%。
对比例1:
取20.9化合物1(0.1mol)和91.71g催化剂PhenoFluorMix(0.15mol)置于800mL甲苯溶液中,在室温下搅拌30分钟,随后加热升温至110℃,恒温搅拌反应30分钟,反应完毕后冷却至室温,过滤,浓缩,硅胶柱色谱纯化,洗脱剂为10%乙醚的正己烷溶液,得到5.7g化合物2(0.027mol),收率27%。
上述实施例为本发明较佳的实施方式,但本发明的实施方式并不受上述实施例的限制,其他的任何未背离本发明的精神实质与原理下所作的改变、修饰、替代、组合、简化,均应为等效的置换方式,都包含在本发明的保护范围之内。
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