GB908964A - Improvements in or relating to the preparation of halogenated benzonitriles and derivatives thereof - Google Patents

Improvements in or relating to the preparation of halogenated benzonitriles and derivatives thereof

Info

Publication number
GB908964A
GB908964A GB756360A GB756360A GB908964A GB 908964 A GB908964 A GB 908964A GB 756360 A GB756360 A GB 756360A GB 756360 A GB756360 A GB 756360A GB 908964 A GB908964 A GB 908964A
Authority
GB
United Kingdom
Prior art keywords
chloro
give
thiocyano
group
iodo
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
Application number
GB756360A
Inventor
Barry Roy John Devlin
John Yates
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shell Research Ltd
Original Assignee
Shell Research Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Shell Research Ltd filed Critical Shell Research Ltd
Priority to GB756360A priority Critical patent/GB908964A/en
Priority to CH834160A priority patent/CH402837A/en
Publication of GB908964A publication Critical patent/GB908964A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
    • C07C331/02—Thiocyanates
    • C07C331/14—Thiocyanates having sulfur atoms of thiocyanate groups bound to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises 2-halo-6-thiocyano-, -iodo-, -diazoborofluoro- and -fluoro-benzonitriles and a process for the preparation of substituted benzonitriles of the general formula <FORM:0908964/IV (b)/1> wherein X represents a halogen atom and Y represents a halogen atom, the diazoborofluoride group N2BF4 or the thiocyano group which comprises treating an aniline derivative of the general formula <FORM:0908964/IV (b)/2> wherein X represents a halogen atom, in solution or suspension in an acid medium, with a diazotising agent and reacting the resulting diazonium salt (a) with concentrated hydrogen fluoride, chloride, bromide or iodide solution to give the corresponding fluoro, chloro, bromo or iodo derivatives, or (b) with a solution of cuprous chloride in hydrochloric acid or cuprous bromide in hydrobromic acid with warming according to Sandemeyer's method, to give the corresponding chloro or bromo derivative, or (c) in the form of the diazonium chloride or bromide with copper bronze or copper powder, according to Gattermann's method, to give the corresponding chloro or bromo derivative, or (d) with aqueous fluoboric acid to give the corresponding diazoborofluorate, or (e) with aqueous fluoboric acid to give the corresponding diazofluoborate, isolating said compound and decomposing it by heating it either alone or in an inert solvent, to give the corresponding fluoro compound, or (f) with cuprous thiocyanate, ferric thiocyanate or a mixture of cuprous or ferric thiocyanate and an alkali metal thiocyanate, in an aqueous medium to give the corresponding thiocyano compound. The examples relate to the preparation of 2-chloro-6-chloro-, iodo-, thiocyano- and fluorobenzonitriles and 2-chloro-benzonitrile-6-diazoborofluoride. The products are employed in pesticidal compositions (see Group VI). Specification 901,977 is referred to.ALSO:Herbicidal compositions comprise a benzonitrile derivative of the formula <FORM:0908964/VI/1> where X represents a halogen atom and Y represents a thiocyano group, a diazoborofluoride group, or a fluorine or iodine atom (see Group IV (b)) and a surface-active agent or a carrier. Specific active substances described include 2-chloro-6-chloro-, -iodo-, -thiocyano-and fluorobenzonitriles.
GB756360A 1959-07-23 1960-03-03 Improvements in or relating to the preparation of halogenated benzonitriles and derivatives thereof Expired GB908964A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB756360A GB908964A (en) 1960-03-03 1960-03-03 Improvements in or relating to the preparation of halogenated benzonitriles and derivatives thereof
CH834160A CH402837A (en) 1959-07-23 1960-07-21 Process for the preparation of benzonitriles

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB756360A GB908964A (en) 1960-03-03 1960-03-03 Improvements in or relating to the preparation of halogenated benzonitriles and derivatives thereof

Publications (1)

Publication Number Publication Date
GB908964A true GB908964A (en) 1962-10-24

Family

ID=9835519

Family Applications (1)

Application Number Title Priority Date Filing Date
GB756360A Expired GB908964A (en) 1959-07-23 1960-03-03 Improvements in or relating to the preparation of halogenated benzonitriles and derivatives thereof

Country Status (1)

Country Link
GB (1) GB908964A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3303092A (en) * 1962-06-29 1967-02-07 Shell Oil Co 1-substituted 2, 6-dihalo phenyl hypnotic and analgesic

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3303092A (en) * 1962-06-29 1967-02-07 Shell Oil Co 1-substituted 2, 6-dihalo phenyl hypnotic and analgesic

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