GB1080167A - Improvements in or relating to the production of halogenated benzene derivatives - Google Patents

Improvements in or relating to the production of halogenated benzene derivatives

Info

Publication number
GB1080167A
GB1080167A GB2387963A GB2387963A GB1080167A GB 1080167 A GB1080167 A GB 1080167A GB 2387963 A GB2387963 A GB 2387963A GB 2387963 A GB2387963 A GB 2387963A GB 1080167 A GB1080167 A GB 1080167A
Authority
GB
United Kingdom
Prior art keywords
lithium
prepared
converted
difluorophenyl
product
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
GB2387963A
Inventor
Roger Anthony Burton
Anthony Maitland Roe
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.)
Smith Kline and French Laboratories Ltd
Original Assignee
Smith Kline and French Laboratories 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 Smith Kline and French Laboratories Ltd filed Critical Smith Kline and French Laboratories Ltd
Priority to GB2387963A priority Critical patent/GB1080167A/en
Priority to GB3594665A priority patent/GB1098387A/en
Publication of GB1080167A publication Critical patent/GB1080167A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/24—Halogenated derivatives
    • C07C39/26—Halogenated derivatives monocyclic monohydroxylic containing halogen bound to ring carbon atoms
    • C07C39/27—Halogenated derivatives monocyclic monohydroxylic containing halogen bound to ring carbon atoms all halogen atoms being bound to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/55—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
    • C07C49/807—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen all halogen atoms bound to the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/15—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction of organic compounds with carbon dioxide, e.g. Kolbe-Schmitt synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic System
    • C07F1/02—Lithium compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

2,6-Dihalogenophenyl lithium compounds are prepared by reacting a m-dihalogenobenzene with a lower alkyl or aryl lithium compound in an inert organic solvent, the temperature of the reaction mixture being maintained at - 50 DEG C. or lower. Other 2,6-dihalogenophenyl compounds are prepared therefrom by conventional methods. In Example 1, n-butyl lithium in tetrahydrofuran is reacted with m-difluorobenzene in tetrahydrofuran, and the solution of m-difluorophenyl lithium obtained is added to a slurry of solid CO2 in ether to form m-difluorobenzoic acid. This is converted via the azide into 2,6-difluoroaniline. In Example 2, 2,6-dichlorobenzoic acid is prepared. In Example 3,2,6-difluorophenyl lithium is treated with N-methyl formanilide at - 50 DEG C. and the product is hydrolysed to 2,6-difluorobenzaldehyde. In Example 4, 2,6-difluorophenyl lithium solution is reacted with trimethyl borate and the product hydrolysed to a boronic or boronic acid derivative which is oxidized by means of H2O2 to 2,6-difluoro-phenol. This is converted to 2-(21,61-difluorophenoxy)-ethylamine by reaction with chloroacetonitrile and reduction of the 2,6-difluorophenoxyacetonitrile formed with lithium aluminium hydride. The amine hydrochloride is refluxed with cyanamide and the product, treated with HNO3, yields 2 - (21,61 - difluorophenoxy)-ethyl guanidine nitrate. In Example 5, 2,6-difluorophenylacetophenone is prepared by the reaction of 2,6-difluorophenyl lithium with acetyl chloride and converted to its oxime. In Example 6, 2,6-difluorobenzoyl chloride and 2,6-difluorobenzamide are prepared from 2,6-difluorobenzoic acid and the amide converted to 2,6-difluorobenzonitrile by means of thionyl chloride.
GB2387963A 1963-06-14 1963-06-14 Improvements in or relating to the production of halogenated benzene derivatives Expired GB1080167A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB2387963A GB1080167A (en) 1963-06-14 1963-06-14 Improvements in or relating to the production of halogenated benzene derivatives
GB3594665A GB1098387A (en) 1963-06-14 1965-08-20 Improvements in or relating to the production of halogenated benzene derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB2387963A GB1080167A (en) 1963-06-14 1963-06-14 Improvements in or relating to the production of halogenated benzene derivatives
GB3594665A GB1098387A (en) 1963-06-14 1965-08-20 Improvements in or relating to the production of halogenated benzene derivatives

Publications (1)

Publication Number Publication Date
GB1080167A true GB1080167A (en) 1967-08-23

Family

ID=26256772

Family Applications (2)

Application Number Title Priority Date Filing Date
GB2387963A Expired GB1080167A (en) 1963-06-14 1963-06-14 Improvements in or relating to the production of halogenated benzene derivatives
GB3594665A Expired GB1098387A (en) 1963-06-14 1965-08-20 Improvements in or relating to the production of halogenated benzene derivatives

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB3594665A Expired GB1098387A (en) 1963-06-14 1965-08-20 Improvements in or relating to the production of halogenated benzene derivatives

Country Status (1)

Country Link
GB (2) GB1080167A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0442340A2 (en) * 1990-02-13 1991-08-21 F. Hoffmann-La Roche Ag Process for the preparation of an organolithium compound starting from 1,3-bis(trifluoromethyl)-benzene

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8331120D0 (en) * 1983-11-22 1983-12-29 Pfizer Ltd Benzaldehyde derivatives
GB9319341D0 (en) * 1993-09-17 1993-11-03 Wellcome Found Novel process
JP5433996B2 (en) * 2008-07-10 2014-03-05 Ｄｉｃ株式会社 Method for producing fluorophenol derivative

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0442340A2 (en) * 1990-02-13 1991-08-21 F. Hoffmann-La Roche Ag Process for the preparation of an organolithium compound starting from 1,3-bis(trifluoromethyl)-benzene
EP0442340A3 (en) * 1990-02-13 1992-01-22 F. Hoffmann-La Roche Ag Process for the preparation of an organolithium compound starting from 1,3-bis(trifluoromethyl)-benzene
US5162577A (en) * 1990-02-13 1992-11-10 Hoffmann-La Roche Inc. Process for lithiation of 1,3-bis(trifluoromethyl)benzene

Also Published As

Publication number Publication date
GB1098387A (en) 1968-01-10

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