GB1503999A - Preparation of halogenated methyl ethyl ethers - Google Patents

Preparation of halogenated methyl ethyl ethers

Info

Publication number
GB1503999A
GB1503999A GBGB50040/75A GB5004075A GB1503999A GB 1503999 A GB1503999 A GB 1503999A GB 5004075 A GB5004075 A GB 5004075A GB 1503999 A GB1503999 A GB 1503999A
Authority
GB
United Kingdom
Prior art keywords
ether
difluoromethyl
trifluoroethyl
chlorine
bromine
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
GBGB50040/75A
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries 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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GBGB50040/75A priority Critical patent/GB1503999A/en
Priority to SE7613545A priority patent/SE7613545L/en
Priority to NO764138A priority patent/NO764138L/no
Priority to FR7636614A priority patent/FR2357510A1/en
Priority to DK544476A priority patent/DK544476A/en
Priority to FI763497A priority patent/FI763497A/fi
Priority to IN2158/CAL/76A priority patent/IN143299B/en
Priority to CA267,244A priority patent/CA1075267A/en
Priority to DE2655196A priority patent/DE2655196A1/en
Priority to JP51146436A priority patent/JPS5271407A/en
Priority to FR7724929A priority patent/FR2351933A1/en
Priority to US05/875,546 priority patent/US4149018A/en
Publication of GB1503999A publication Critical patent/GB1503999A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/04—Saturated ethers
    • C07C43/12—Saturated ethers containing halogen
    • C07C43/123—Saturated ethers containing halogen both carbon chains are substituted by halogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

1503999 Production of halogenated methyl ethyl ether IMPERIAL CHEMICAL INDUSTRIES Ltd 1 Dec 1976 [5 Dec 1975] 50040/75 Heading C2C A process for the manufacture of difluoromethyl 1,2,2-trifluoroethyl ether comprises either the reduction of a compound of the formula wherein X is hydrogen, chlorine or bromine, and wherein either Y and Z, which may be the same or different, each is hydrogen, chlorine or bromine, provided that X, Y and Z are not all hydrogen, or wherein Y and Z are joined together to form an olefinic bond between the two carbon atoms; or the fluorination of a compound of the formula wherein X<SP>2</SP>, X<SP>3</SP>, Z<SP>1</SP> and Z<SP>2</SP>, which may be the same or different, each is fluorine, chlorine or bromine and wherein Y<SP>2</SP> is hydrogen, fluorine, chlorine or bromine, provided that X<SP>2</SP>, X<SP>3</SP>, Y<SP>1</SP>, Z<SP>1</SP> and Z<SP>2</SP> are not all fluorine. The following intermediate compounds are prepared in the examples: 1,2 - Dichloro - 1,2,2 - trifluoroethyl difluoromethyl ether by treating 1,2-dieh1oro-1,2,2-trifluoroethyl methyl ether with chlorine under radiation (Example 1). Difluoromethyl - 1,2,2 - trifluorovinyl ether by treating 1,2 - dichloro - 1,2,2 - trifluoroethyl difluoromethyl ether with Zn/ZnCl 2 in dimethylsulphoxide (Example 2). (1 - Chloro -, 2 - chloro - and 1,2 - dichloro- 1,2,2 - trifluoroethyl difluoromethyl ethers by treating difluoromethyl - 1,2,2 - trifluorovinyl ether with HCl (Example 4). Difluoromethyl - (1 - bromo - or 2 - bromo -)- 1,2,2-trifluoroethyl ether by treating difluoromethyl 1,2,2-trifluorovinyl ether with HBr (Example 9). Methyl 1,2,2-trifluoroethyl ether by reducing 1,2,2-trifluorovinyl ether in the presence of a palladium/carbon catalyst (Example 10). The following intermediate compounds are claimed per se:
GBGB50040/75A 1975-12-05 1975-12-05 Preparation of halogenated methyl ethyl ethers Expired GB1503999A (en)

Priority Applications (12)

Application Number Priority Date Filing Date Title
GBGB50040/75A GB1503999A (en) 1975-12-05 1975-12-05 Preparation of halogenated methyl ethyl ethers
SE7613545A SE7613545L (en) 1975-12-05 1976-12-02 METHOD OF PREPARING DIFLUOROMETHYL-1,2,2-TRIFLNORETHYLETHER
NO764138A NO764138L (en) 1975-12-05 1976-12-03
FR7636614A FR2357510A1 (en) 1975-12-05 1976-12-03 PROCESS FOR PREPARING A DIFLUOROMETHYL ETHER AND 1,2,2-TRIFLUORETHYL AND PRODUCT OBTAINED
DK544476A DK544476A (en) 1975-12-05 1976-12-03 PROCEDURE FOR THE PREPARATION OF DIFLUOROMETHYL-1,2,2-TRIFLUOROETHYLETHER
FI763497A FI763497A (en) 1975-12-05 1976-12-03
IN2158/CAL/76A IN143299B (en) 1975-12-05 1976-12-04
CA267,244A CA1075267A (en) 1975-12-05 1976-12-06 Process for the manufacture of difluoromethyl 1,2,2-trifluoromethyl ether
DE2655196A DE2655196A1 (en) 1975-12-05 1976-12-06 PROCESS FOR PREPARING THE COMPOUND DIFLUOROMETHYL-1,2,2-TRIFLUOROAETHYL-AETHER
JP51146436A JPS5271407A (en) 1975-12-05 1976-12-06 Method of producing difluoromethl 1*2*22 trifluoroethylethel
FR7724929A FR2351933A1 (en) 1975-12-05 1977-08-12 PROCESS FOR PREPARATION OF A DIFLUOROMETHYL ETHER AND 1,2,2-TRIFLUORETHYL BY FLUORATION
US05/875,546 US4149018A (en) 1975-12-05 1978-02-06 Compound CHCl2 -O-CHF-CHF2

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GBGB50040/75A GB1503999A (en) 1975-12-05 1975-12-05 Preparation of halogenated methyl ethyl ethers

Publications (1)

Publication Number Publication Date
GB1503999A true GB1503999A (en) 1978-03-15

Family

ID=10454426

Family Applications (1)

Application Number Title Priority Date Filing Date
GBGB50040/75A Expired GB1503999A (en) 1975-12-05 1975-12-05 Preparation of halogenated methyl ethyl ethers

Country Status (10)

Country Link
JP (1) JPS5271407A (en)
CA (1) CA1075267A (en)
DE (1) DE2655196A1 (en)
DK (1) DK544476A (en)
FI (1) FI763497A (en)
FR (2) FR2357510A1 (en)
GB (1) GB1503999A (en)
IN (1) IN143299B (en)
NO (1) NO764138L (en)
SE (1) SE7613545L (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2044263A (en) * 1979-03-12 1980-10-15 Airco Inc Reduction of halogenated ethers

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1130322A (en) * 1979-04-25 1982-08-24 Airco, Inc. Method for the dehalogenation of ethers
US11111196B2 (en) * 2017-11-09 2021-09-07 Kanto Denka Kogyo Co., Ltd. 1,2-dichloro-1-(2,2,2-trifluoroethoxy)ethylene, production method therefor, and uses thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3461213A (en) * 1966-10-03 1969-08-12 Air Reduction 1,1 difluoro-2,2-dichloroethyl difluoromethyl ether or an anesthetic agent
GB1499818A (en) * 1974-12-06 1978-02-01 Ici Ltd Anaesthetic composition

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2044263A (en) * 1979-03-12 1980-10-15 Airco Inc Reduction of halogenated ethers

Also Published As

Publication number Publication date
NO764138L (en) 1977-06-07
FR2357510A1 (en) 1978-02-03
SE7613545L (en) 1977-06-06
JPS5271407A (en) 1977-06-14
IN143299B (en) 1977-10-29
CA1075267A (en) 1980-04-08
DK544476A (en) 1977-06-06
FR2351933B1 (en) 1981-01-09
FR2351933A1 (en) 1977-12-16
DE2655196A1 (en) 1977-06-16
FI763497A (en) 1977-06-06

Similar Documents

Publication Publication Date Title
JPS5687599A (en) E 55 22halogenovinyl arabinofuranosyluracil and its preparation
CA2015247A1 (en) Process for preparing fluoroalkyl vinyl compound
ES8404783A1 (en) New 2-((2,6-dichlorophenyl)amine)phenylacetoxyacetyl derivatives, the process for preparing the same and their use in therapeutics.
GB1503999A (en) Preparation of halogenated methyl ethyl ethers
JPS57118535A (en) Preparation of fluoroalkyl alpha-chloroacrylate
GB1273914A (en) Process for the production of fluorinated nitrogen heterocycles
GB1499818A (en) Anaesthetic composition
JPS5340737A (en) Preparation of cyanophenol
GB1362959A (en) Phosphorus-containing unsaturated carboxylic acid derivatives
GB1471639A (en) Diphenyl ether derivatives
DE3462031D1 (en) Alpha,alpha-dimethylphenylacetanilide derivatives, process for production thereof, and use thereof as insecticide
JPS5721321A (en) Antihyperlipemic agent
PH19573A (en) Process and intermediates for preparation of 1,1-dixopenicillanoyloxymethyl 6-beta aminopenicillanate
JPS5219620A (en) Process for preparation of 2- hydroxyalkylacrylate
AU571079B2 (en) Preparing 3-cyano-4-amino aceto phenones
ES479058A1 (en) Procedure for preparing naftalene derivatives. (Machine-translation by Google Translate, not legally binding)
JPS5334705A (en) Preparation of bromotrifluoromethane
JPS5239697A (en) Synthesis of l-and dl-p-n-butoxybenzyl- 6,7-dehydrohyosciaminium bromi de
JPS5517335A (en) 5-fluoro-6-hydroxy-6-carboxy-5,6-dihydro-uracil and its preparation
JPS5268109A (en) Preparation of perfluoroisopropyl iodide
JPS5321119A (en) Preparation of azodicarbonamide
GB1505584A (en) Production of 1,1-dichloro-4-methylpenta-1,3-diene by an oxidative coupling process
GB1038695A (en) Process for the manufacture of difluorochlorobromomethane
JPS51127029A (en) Process for preparation of o-alkoxy-p- allylphenol
JPS52118468A (en) Purification of imidazole derivatives by means of ion-exchange resin

Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee