1-溴-2,4-二氯-5-氟苯 | 1481-63-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-溴-2,4-二氯-5-氟苯
• 中文别名: 5-溴-2,4-二氯氟苯；2,4-二氯-5-氟溴苯
• 英文名称: 2,4-dichloro-5-bromofluorobenzene
• 英文别名: 2,4-dichloro-5-fluorobromobenzene；6-Brom-3,5-dichlor-2-fluor-benzol；1-Fluor-2,4-dichlor-5-brombenzol；1-bromo-2,4-dichloro-5-fluorobenzene；5-bromo-2,4-dichlorofluorobenzene
• CAS: 1481-63-6
• 化学式: C₆H₂BrCl₂F
• 分子量: 243.89
• InChiKey: HNCWLJLWAVCZDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  1-溴-2,4-二氯-5-氟苯 在 氯 作用下， 生成 1,2,4-三氯-5-氟苯
  参考文献：
  名称：

  Vorozhtsov,N.N. et al., Journal of general chemistry of the USSR, 1961, vol. 31, p. 1561 - 1564

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4-二氯氟苯 在 iron(III) chloride 、 溴 作用下， 以 二氯甲烷 为溶剂， 以247 g的产率得到1-溴-2,4-二氯-5-氟苯
  参考文献：
  名称：

  一种2，4，5-三氟苯乙酸及其中间体的制备方法

  摘要：

  本发明涉及有机合成技术领域，具体涉及一种2，4，5‑三氟苯乙酸及其中间体的制备方法。2，4，5‑三氟苯乙酸的中间体I包括：1)将2，4‑二氯氟苯进行溴化反应，制备获得2，4‑二氯‑5‑溴氟苯；2)将步骤1)制备获得的2，4‑二氯‑5‑溴氟苯进行格氏、酰基化反应，制备获得2，4‑二氯‑5‑氟苯甲醛；3)将步骤2)制备获得的2，4‑二氯‑5‑氟苯甲醛进行氟化反应，制备获得2，4，5‑三氟苯乙酸的中间体I。本发明避免了高危险性的硝化、重氮化反应，和高污染、选择性差的氯甲基化反应，以及各种低转化率的工艺，获得了全新的制备工艺，提高了规模化生产的可操作性和安全性。

  公开号：

  CN115677477A

文献信息

• Process for preparing biphenyls using palladacycles as catalysts
  申请人：Hoechst AG

  公开号：US05559277A1

  公开（公告）日：1996-09-24

  The invention relates to a process for preparing biphenyls of the formula (I) ##STR1## where R.sup.1a to R.sup.10a are, independently of one another, hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.1 -C.sub.12 -alkenyl, C.sub.1 -C.sub.12 -alkynyl, alkoxy-(C.sub.1 -C.sub.12), acyloxy-(C.sub.1 -C.sub.12), O-phenyl, aryl, heteroaryl, fluorine, chlorine, OH, NO.sub.2, CN, COOH, CHO, SO.sub.3 H, SO.sub.2 R, SOR, NH.sub.2, NH-alkyl-(C.sub.1 -C.sub.12), N-alkyl.sub.2 -(C.sub.1 -C.sub.12), C-Hal.sub.3, NHCO-alkyl-(C.sub.1 -C.sub.8), CONH-alkyl-(C.sub.1 -C.sub.4), CON-(alkyl).sub.2 -(C.sub.1 -C.sub.4), COO-alkyl-(C.sub.1 -C.sub.12), CONH.sub.2, CO-alkyl-(C.sub.1 -C.sub.12), NHCOH, NHCOO-alkyl-(C.sub.1 -C.sub.8), CO-phenyl, COO-phenyl, CHCHCO.sub.2 -alkyl-(C.sub.1 -C.sub.12), CHCHCO.sub.2 H, PO-phenyl.sub.2, PO-alkyl.sub.2 -(C.sub.1 -C.sub.8), by reaction of haloaromatics or aryl sulfonates of the formula (II) ##STR2## with arylboron derivatives of the formula III ##STR3## where R.sup.1a to R.sup.10a are as defined above and X is bromine, chlorine or OSO.sub.2 CF.sub.3, OSO.sub.2 -aryl, OSO.sub.2 -alkyl and Y is B(OH).sub.2, B(O-alkyl).sub.2, B(O-aryl).sub.2, wherein a palladium compound of the formula (IV) ##STR4## where R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 are, independently of one another, hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.5 -C.sub.8)-cycloalkyl, (C.sub.1 -C.sub.4)-alkoxy, fluorine, NH.sub.2, NH-alkyl(C.sub.1 -C.sub.4), N(alkyl).sub.2 -(C.sub.1 -C.sub.4), CO.sub.2 -alkyl-(C.sub.1 -C.sub.4), OCO-alkyl-(C.sub.1 -C.sub.4) or phenyl, or R.sup.1 and R.sup.2, R.sup.2 and R.sup.3, R.sup.3 and R.sup.4, R.sup.5 and R.sup.6 together form an aliphatic or aromatic ring, and R.sup.7, R.sup.8 are (C.sub.1 -C.sub.8)-alkyl, (C.sub.3 -C.sub.12)-cycloalkyl, substituted or unsubstituted aryl and Y is an anion of an inorganic or organic acid, is used as catalyst.

  该发明涉及一种制备式(I)的联苯的方法##STR1##其中R.sup.1a至R.sup.10a分别独立地是氢、C.sub.1-C.sub.12-烷基、C.sub.1-C.sub.12-烯基、C.sub.1-C.sub.12-炔基、烷氧基-(C.sub.1-C.sub.12)、酰氧基-(C.sub.1-C.sub.12)、O-苯基、芳基、杂芳基、氟、氯、羟基、硝基、氰基、羧基、醛基、磺酸基、磺酰基、磺氧基、氨基、氨基烷基-(C.sub.1-C.sub.12)、N-烷基.sub.2-(C.sub.1-C.sub.12)、C-Hal.sub.3、NHCO-烷基-(C.sub.1-C.sub.8)、CONH-烷基-(C.sub.1-C.sub.4)、CON-(烷基).sub.2-(C.sub.1-C.sub.4)、COO-烷基-(C.sub.1-C.sub.12)、CONH.sub.2、CO-烷基-(C.sub.1-C.sub.12)、NHCOH、NHCOO-烷基-(C.sub.1-C.sub.8)、CO-苯基、COO-苯基、CHCHCO.sub.2-烷基-(C.sub.1-C.sub.12)、CHCHCO.sub.2 H、PO-苯基.sub.2、PO-烷基.sub2-(C.sub.1-C.sub.8)，通过式(II)的卤代芳烃或芳基磺酸盐与式III的芳基硼衍生物的反应##STR2##其中R.sup.1a至R.sup.10a如上定义，X为溴、氯或OSO.sub.2 CF.sub.3、OSO.sub.2-芳基、OSO.sub.2-烷基，Y为B(OH).sub.2、B(O-烷基).sub.2、B(O-芳基).sub.2，其中式(IV)的钯化合物##STR4##其中R.sup.1、R.sup.2、R.sup.3、R.sup.4、R.sup.5、R.sup.6独立地是氢、(C.sub.1-C.sub.4)-烷基、(C.sub.5-C.sub.8)-环烷基、(C.sub.1-C.sub.4)-烷氧基、氟、NH.sub.2、NH-烷基(C.sub.1-C.sub.4)、N(烷基).sub.2-(C.sub.1-C.sub.4)、CO.sub.2-烷基-(C.sub.1-C.sub.4)、OCO-烷基-(C.sub.1-C.sub.4)或苯基，或R.sup.1和R.sup.2、R.sup.2和R.sup.3、R.sup.3和R.sup.4、R.sup.5和R.sup.6一起形成脂肪族或芳香族环，R.sup.7、R.sup.8是(C.sub.1-C.sub.8)-烷基、(C.sub.3-C.sub.12)-环烷基、取代或未取代的芳基，Y是无机或有机酸的阴离子，用作催化剂。
• Halogenated cinnamic acids and esters thereof, processes for the
  申请人：Hoechst Aktiengesellschaft

  公开号：US05516932A1

  公开（公告）日：1996-05-14

  The present invention relates to compounds of the formula ##STR1## in which R.sup.1 and R.sup.2 are identical or different and are hydrogen or an alkyl radical having 1 to 18 carbon atoms and optionally containing oxygen, nitrogen or halogen, the radicals X, Y and Z are identical and are a fluorine, bromine or iodine atom or if two of the radicals X, Y or Z are identical or all of the radicals X, Y, Z are different from each other, X, Y and Z are a fluorine, chlorine, bromine or iodine atom. The invention further relates to a process for the preparation of the compounds, by reacting an aryldiazonium salt of the formula ##STR2## in which the radicals X, Y and Z are identical and are a fluorine, bromine or iodine atom or, if two of the radicals X, Y and Z are identical or all of the radicals X, Y, Z are different from each other, X, Y and Z are a fluorine, chlorine, bromine or iodine atom and A.sup.(-) is an anion of an acid having a pK.sub.a <7, with a compound of the formula ##STR3## in which R.sup.1 and R.sup.2 are identical or different and are hydrogen or an alkyl radical having 1 to 18 carbon atoms and optionally containing oxygen, nitrogen or halogen, in the presence of a palladium-containing catalyst, if appropriate with addition of a base, and the aryldiazonium salts of the formula (II).

  本发明涉及以下结构的化合物：其中R.sup.1和R.sup.2相同或不同，为氢或具有1至18个碳原子的烷基基团，可能含有氧、氮或卤素；基团X、Y和Z相同，为氟、溴或碘原子，或者如果基团X、Y或Z中有两个相同，或者所有基团X、Y、Z互不相同，则X、Y和Z为氟、氯、溴或碘原子。本发明还涉及一种制备这些化合物的方法，通过将以下结构的芳基重氮盐与以下结构的化合物反应而制备：其中基团X、Y和Z相同，为氟、溴或碘原子，或者如果基团X、Y和Z中有两个相同，或者所有基团X、Y、Z互不相同，则X、Y和Z为氟、氯、溴或碘原子，A.sup.(-)为具有pK.sub.a<7的酸的阴离子，存在钯催化剂的情况下，必要时加入碱，以及结构(II)的芳基重氮盐。
• Process for the preparation of 2,4-dichloro-5-fluorobenzonitrile
  申请人：Hoechst Aktiengesellschaft

  公开号：US05187295A1

  公开（公告）日：1993-02-16

  Process for the preparation of 2,4-dichloro-5-fluorobenzonitrile, by reacting 5-bromo-2,4-dichlorofluorobenzene with about 10 to about 300 mol % of copper(I) cyanide in the presence of about 10 to about 2,000 mol % of a polar aprotic solvent at temperatures from about 100.degree. to about 250.degree. C. to give 2,4-dichloro-5-fluorobenzonitrile.

  通过在存在约10至约300摩尔％的氰化铜(I)的情况下，将5-溴-2,4-二氯氟苯与约10至约2000摩尔％的极性无质子溶剂在约100至约250摄氏度的温度下反应，制备2,4-二氯-5-氟苯甲腈的过程。
• Catalyst for nucleophilic aromatic substitutions
  申请人：Hoechst AG

  公开号：US05492875A1

  公开（公告）日：1996-02-20

  A catalyst consisting essentially of a quaternary ammonium compound, comprising at least one linear or branched alkoxypolyoxyalkyl chain, and a quaternary ammonium or phosphonium salt or a polyether, or a mixture of each of the specified compounds, is suitable for accelerating, or making possible for the first time, many nucleophilic aromatic substitutions.

  一个催化剂主要由季铵化合物组成，其中至少包括一条线性或支链烷氧基聚氧烷链，以及一种季铵盐或磷铵盐或聚醚，或上述化合物的混合物，适用于加速，或首次实现许多亲核芳香取代反应。
• Processes for producing 5-fluorbenzoic acids and their intermediates
  申请人：ASAHI GLASS COMPANY LTD.

  公开号：EP0431373A2

  公开（公告）日：1991-06-12

  A process for producing a 5-fluorobenzoic acid of the formula (V), which comprises trichloromethylating a fluorobenzene of the formula (I) to obtain a 5-fluorobenzotrichloride of the formula (II), then reacting it with aqueous ammonia to obtain a 5-fluorobenzonitrile of the formula (III), reacting it with a fluorinating agent to obtain a 5-fluorobenzonitrile of the formula (IV) and hydrolyzing it: wherein each of X₁ , X₃, Y₁ and Y₃ is a halogen atom, and each of X₂ and Y₂ is hydrogen or a halogen atom.

  一种生产式(V)的5-氟苯甲酸的工艺，包括将式(I)的氟苯三氯甲基化，得到式(II)的5-氟三氯甲苯，然后与水氨反应，得到式(III)的5-氟苯腈，再与氟化剂反应，得到式(IV)的5-氟苯腈，并将其水解： 其中 X₁、X₃、Y₁ 和 Y₃ 各为卤原子，X₂ 和 Y₂ 各为氢或卤原子。