EP1863783A4 - Improved process for preparing insecticidal (disubstitutedpropenyl) phenylalkyl substituted dihydrobenzofurans - Google Patents

Improved process for preparing insecticidal (disubstitutedpropenyl) phenylalkyl substituted dihydrobenzofurans

Info

Publication number
EP1863783A4
EP1863783A4 EP06739229A EP06739229A EP1863783A4 EP 1863783 A4 EP1863783 A4 EP 1863783A4 EP 06739229 A EP06739229 A EP 06739229A EP 06739229 A EP06739229 A EP 06739229A EP 1863783 A4 EP1863783 A4 EP 1863783A4
Authority
EP
European Patent Office
Prior art keywords
formula
compound
disubstitutedpropenyl
halogen
substituted
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.)
Withdrawn
Application number
EP06739229A
Other languages
German (de)
French (fr)
Other versions
EP1863783A1 (en
Inventor
Jaidev S Goudar
Charles E Hatch Iii
Guozhi Wang
Russell Patera
Craig A Polsz
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.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
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 Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1863783A1 publication Critical patent/EP1863783A1/en
Publication of EP1863783A4 publication Critical patent/EP1863783A4/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring

Definitions

  • This invention is in the field of chemical processes; more specifically, an improved process for preparing (disubstitutedpropenyl) phenylalkyl substituted dihydrobenzofurans.
  • R 3 R , R 3 , R , R 5 and R 6 are independently selected from halogen or alkyl and x is 2, 3, 4, 5 or 6; are useful insecticides and have been described in U.S. Patent number 6,987,194, the disclosure of which is incorporated herein by reference. Disadvantages of processes to produce these compounds include less than optimal yields, less than optimal cycle times and high catalyst loadings.
  • the present invention improves the process for preparing substituted phenolylalkyl substituted dihydrobenzofurans of formula I.
  • overall yield, cycle times and catalyst loading are improved for the production of (disubstitutedpropenyl) phenylalkyl substituted dihydrobenzofurans.
  • R 3 and R are selected from halogen
  • R 5 and R are independently selected from halogen or alkyl; and x is 2, 3, 4, 5 or 6;
  • R 5 and R 6 are as defined above;
  • R 7 and R 8 are independently selected from halogen, hydroxyl or -OSO 2 R 9 wherein R 9 is alkyl or aryl; and x is 2, 3, 4, 5 or 6;
  • R 5 R R and x are as defined above;
  • R and R 4 are as defined above;
  • the "about” range shall be not more than 10% of the absolute value of an end point or 10% of the range recited, whichever is less.
  • alkyl As used in this specification and unless otherwise indicated the substituent terms "alkyl”, “alkoxy”, and “haloalkyl”, used alone or as part of a larger moiety, includes straight or branched chains of at least one or two carbon atoms, as appropriate to the substituent, and preferably up to 12 carbon atoms, more preferably up to ten carbon atoms, most preferably up to seven carbon atoms.
  • Halogen “halide” or “halo” refers to fluorine, bromine, iodine, or chlorine.
  • ambient temperature refers to a temperature in the range of about 20° C to about 30° C. Certain solvents, catalysts, and the like are known by their acronyms.
  • DMAC N,N-dimethylacetarnide
  • DMF N,N-dimethylformamide
  • THF tetrahydrofuran
  • glymes refers to a class of solvents comprised of monoglyme, diglyme, triglyme, tetraglyme, and polyglyme.
  • the present invention relates to a process for preparing a substituted phenolylalkyl substituted dihydrobenzofuran of formula I:
  • R and R are selected from halogen
  • R 5 and R 6 are independently selected from halogen or alkyl; and x is 2, 3, 4, 5 or 6;
  • R 7 and R 8 are independently selected from halogen, hydroxyl or -OSO 2 R 9 wherein R 9 is alkyl or aryl; and x is 2, 3, 4, 5 or 6;
  • R 5 , R 6 R 8 and x are as defined above;
  • R 3 and R 4 are as defined above;
  • the reaction of step a) can be conducted in the presence of a catalyst; at elevated temperature.
  • the catalyst can be polyethylene glycol, dimethylaminopyridine, triethylamine, pyridine, potassium iodide, phase transfer catalysts such as quaternary ammonium salts or quaternary phosphonium salts or mixtures thereof.
  • the catalyst can be present in a concentration of from about 0.1% by weight to about 15% by weight.
  • the elevated temperature can be in the range of 30°C to 120°C.
  • the reaction of step b) can be conducted in the presence of a solvent; in the presence of a catalyst; at elevated temperature.
  • the solvent can be tetrahydrofuran, toluene, xylene, 1 ,2-dichloroethane, triethylamine, />-dioxane, N 5 N- dimethylacetamide, N,N-dimethylformamide, glymes, methyl isobutyl ketone, dimethylsulfoxide or mixtures thereof.
  • the catalyst can be polyethylene glycol, potassium iodide, dimethylaminopyridine, triethylamine, pyridine, phase transfer catalysts such as quaternary ammonium salts or quaternary phosphonium salts or mixtures thereof.
  • the catalyst can be present in a concentration of from about 0.1% by weight to about 20% by weight.
  • the elevated temperature can be in the range of 30°C to 70°C.
  • Another embodiment of the present invention is a compound of formula II:
  • R 5 and R 6 are independently selected from halogen or alkyl;
  • R 8 is selected from halogen, hydroxyl or -OSO 2 R 9 wherein R 9 is alkyl or aryl; and
  • x is 2, 3, 4, 5 or 6.
  • the following example illustrates a process for preparing substituted phenolylalkyl substituted dihydrobenzofurans of formula I.
  • R 5 and R 6 are alkyl wherein R 7 and R 8 are halogen ⁇
  • step (b) of Example 1 2,6-dihalo-4-(phenylmethoxy)phenol, a compound of formula (C), was reacted with a l-(2,2-dialkyl(2,3-dihydrobenzo[2,3-b]furan-7- yloxy))-4-haloalkane, a compound of formula II, for example l-(2,2-dialkyl(2,3- dihydrobenzo[2,3-b]furan-7-yloxy))-4-halobutane, in the presence of abase, a solvent and a catalyst at elevated temperature to form a 2-[4-(2,2-dialkyl(2,3- dihydrobenzo[2,3-b]furan-7-yloxy))alkoxy]-l,3-dihalo-5-(phenylmethoxy)benzene, a compound of formula I, for example 2-[4-(2,2-dialkyl(2,3-dihydrobenzo[2,3- b]fur

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Furan Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

An improved process is described for preparing (disubstitutedpropenyl) phenylalkyl substituted dihydrobenzoforans. This improved process is focused on steps to produce key intermediates, namely substituted phenolylalkyl substituted dihydrobenzofurans of formula (I) where R3, R4, R5, R6 and x are defined herein.

Description

Improved Process for Preparing Insecticidal (Disubstitutedpropenyl) Phenylalkyl Substituted Dihydrobenzofurans
This application claims the benefit of U.S. Provisional Application No. 60/664,427, filed March 23, 2005.
Field of the Invention:
This invention is in the field of chemical processes; more specifically, an improved process for preparing (disubstitutedpropenyl) phenylalkyl substituted dihydrobenzofurans.
Backgound:
(Disubstitutedpropenyl) phenylalkyl substituted dihydrobenzofurans, such as:
wherein R 3 R , R3, R , R5 and R6 are independently selected from halogen or alkyl and x is 2, 3, 4, 5 or 6; are useful insecticides and have been described in U.S. Patent number 6,987,194, the disclosure of which is incorporated herein by reference. Disadvantages of processes to produce these compounds include less than optimal yields, less than optimal cycle times and high catalyst loadings. Compounds known as substituted phenolylalkyl substituted dihydrobenzofurans, represented by formula I:
Formula I wherein R >3 , τ R>4 , R r> 5 , r R> 6 and x are as defined above; are key intermediates in the process for preparing (disubstitutedpropenyl) phenylalkyl substituted dihydrobenzofurans as described in U.S. Patent number 6,987,194.
Summary of the Invention
The present invention improves the process for preparing substituted phenolylalkyl substituted dihydrobenzofurans of formula I. As a result of the present invention, overall yield, cycle times and catalyst loading are improved for the production of (disubstitutedpropenyl) phenylalkyl substituted dihydrobenzofurans. Specifically, it has now been found that a substituted phenolylalkyl substituted dihydrobenzofuran of formula I:
Formula I wherein
R3 and R are selected from halogen;
R5 and R are independently selected from halogen or alkyl; and x is 2, 3, 4, 5 or 6;
can be prepared in excellent yield and purity by a process comprising: a) reacting a compound of formula (A):
Formula (A)
wherein R5 and R6 are as defined above;
with a compound of formula (B):
R7^(CH2)X \ R
Formula (B) wherein
R7 and R8 are independently selected from halogen, hydroxyl or -OSO2R9 wherein R9 is alkyl or aryl; and x is 2, 3, 4, 5 or 6;
in the presence of a base to form a compound of formula II:
R8— (CH2)
Formula II
wherein
R 5 R R and x are as defined above; and
b) reacting a compound of formula (C):
wherein R and R4 are as defined above;
with a compound of formula II in the presence of a base to form a compound of formula I.
Definitions
The modifier "about" is used herein to indicate that certain preferred operating ranges, such as ranges for molar ratios for reactants, material amounts, and temperature, are not fixedly determined. The meaning will often be apparent to one of ordinary skill. For example, a recitation of a temperature range of about 120° C to about 135° C in reference to, for example, an organic chemical reaction would be interpreted to include other like temperatures that can be expected to favor a useful reaction rate for the reaction, such as 105° C or 150° C. Where guidance from the experience of those of ordinary skill is lacking, guidance from the context is lacking, and where a more specific rule is not recited below, the "about" range shall be not more than 10% of the absolute value of an end point or 10% of the range recited, whichever is less.
As used in this specification and unless otherwise indicated the substituent terms "alkyl", "alkoxy", and "haloalkyl", used alone or as part of a larger moiety, includes straight or branched chains of at least one or two carbon atoms, as appropriate to the substituent, and preferably up to 12 carbon atoms, more preferably up to ten carbon atoms, most preferably up to seven carbon atoms. "Halogen", "halide" or "halo" refers to fluorine, bromine, iodine, or chlorine. The term "ambient temperature" refers to a temperature in the range of about 20° C to about 30° C. Certain solvents, catalysts, and the like are known by their acronyms. These include the acronyms "DMAC" meaning N,N-dimethylacetarnide, "DMF" meaning N,N-dimethylformamide, "THF" meaning tetrahydrofuran. The term "glymes" refers to a class of solvents comprised of monoglyme, diglyme, triglyme, tetraglyme, and polyglyme.
Detailed Description of the Invention
The present invention relates to a process for preparing a substituted phenolylalkyl substituted dihydrobenzofuran of formula I:
Formula I wherein
R and R are selected from halogen;
R5 and R6 are independently selected from halogen or alkyl; and x is 2, 3, 4, 5 or 6;
said process comprising:
a) reacting a compound of formula (A):
Formula (A) wherein R and R are as defined above;
with a compound of formula (B):
R7^(CH2)χ \R8
Formula (B) wherein
R7 and R8 are independently selected from halogen, hydroxyl or -OSO2R9 wherein R9 is alkyl or aryl; and x is 2, 3, 4, 5 or 6;
in the presence of a base to form a compound of formula II:
Formula II wherein
R5, R6 R8 and x are as defined above; and
reacting a compound of formula (CJ:
Formula (C)
wherein R3 and R4 are as defined above;
with a compound of formula II in the presence of a base to form a compound of formula I.
The reaction of step a) can be conducted in the presence of a catalyst; at elevated temperature. The catalyst can be polyethylene glycol, dimethylaminopyridine, triethylamine, pyridine, potassium iodide, phase transfer catalysts such as quaternary ammonium salts or quaternary phosphonium salts or mixtures thereof. The catalyst can be present in a concentration of from about 0.1% by weight to about 15% by weight. The elevated temperature can be in the range of 30°C to 120°C. The reaction of step b) can be conducted in the presence of a solvent; in the presence of a catalyst; at elevated temperature. The solvent can be tetrahydrofuran, toluene, xylene, 1 ,2-dichloroethane, triethylamine, />-dioxane, N5N- dimethylacetamide, N,N-dimethylformamide, glymes, methyl isobutyl ketone, dimethylsulfoxide or mixtures thereof. The catalyst can be polyethylene glycol, potassium iodide, dimethylaminopyridine, triethylamine, pyridine, phase transfer catalysts such as quaternary ammonium salts or quaternary phosphonium salts or mixtures thereof. The catalyst can be present in a concentration of from about 0.1% by weight to about 20% by weight. The elevated temperature can be in the range of 30°C to 70°C. Another embodiment of the present invention is a compound of formula II:
Formula II wherein R5 and R6 are independently selected from halogen or alkyl; R8 is selected from halogen, hydroxyl or -OSO2R9 wherein R9 is alkyl or aryl; and x is 2, 3, 4, 5 or 6.
The following example illustrates a process for preparing substituted phenolylalkyl substituted dihydrobenzofurans of formula I.
Example
wherein R5 and R6 are alkyl wherein R7 and R8 are halogen π
are alkyl
a) Base/Catalyst/30°C to 120°C/4-8 hours b) Base/Catalyst/Solvent/30°C to 70°C/6-12 hours
In the first step (a) of Example 1, 2,2-dialkyl-2,3-dihydrobenzo[b]furan-7-ol, a compound of formula (A), was reacted with a 1,4-dihaloalkane, a compound of formula (B), for example 1 ,4-dihalobutane, in the presence of abase and a catalyst at elevated temperature to form a l-(2,2-dialkyl(2,3-dihydfobenzo[2,3-b]furan-7- yloxy))-4-haloalkane, a compound of formula II, for example l-(2,2-dialkyl(2,3- dihydrobenzo[2,3-b]furan-7-yloxy))-4-halobutane.
In step (b) of Example 1, 2,6-dihalo-4-(phenylmethoxy)phenol, a compound of formula (C), was reacted with a l-(2,2-dialkyl(2,3-dihydrobenzo[2,3-b]furan-7- yloxy))-4-haloalkane, a compound of formula II, for example l-(2,2-dialkyl(2,3- dihydrobenzo[2,3-b]furan-7-yloxy))-4-halobutane, in the presence of abase, a solvent and a catalyst at elevated temperature to form a 2-[4-(2,2-dialkyl(2,3- dihydrobenzo[2,3-b]furan-7-yloxy))alkoxy]-l,3-dihalo-5-(phenylmethoxy)benzene, a compound of formula I, for example 2-[4-(2,2-dialkyl(2,3-dihydrobenzo[2,3- b]furan-7-yloxy))butoxy]-l ,3-dihalo-5-(phenylmethoxy)benzene.
While this invention has been described with an emphasis upon preferred embodiments, it will be obvious to those of ordinary skill in the art that variations of the preferred embodiments may be used and that it is intended that the invention may be practiced otherwise than as specifically described herein. Accordingly this invention includes all modifications encompassed within the spirit and scope as defined by the following claims.

Claims

What is claimed is:
1. A process for preparing a compound of formula I:
Formula I wherein
R3 and R4 are selected from halogen;
R5 and R6 are independently selected from halogen or alkyl; and x is 2, 3, 4, 5 or 6;
said process comprising:
a) reacting a compound of formula (A):
Formula (A)
wherein R5 and R6 are as defined above;
with a compound of formula (B):
Formula (B) wherein *7 fi
R and R are independently selected from halogen, hydroxyl or -OSO2R9 wherein R9 is alkyl or aryl; and x is 2, 3, 4, 5 or 6;
in the presence of a base to form a compound of formula II:
Formula II
wherein R , R R and x are as defined above; and
reacting a compound of formula (C):
wherein R and R are as defined above;
with a compound of formula II in the presence of a base to form a compound of formula I. 2. The process of claim 1 wherein the reacting of step a) is conducted in the presence of a catalyst.
3. The process of claim 1 wherein the reacting of step a) is conducted at elevated temperature.
4. The process of claim 1 wherein the reacting of step b) is conducted in the presence of a solvent.
5. The process of claim 1 wherein the reacting of step b) is conducted in the presence of a catalyst.
6. The process of claim 1 wherein the reacting of step b) is conducted at elevated temperature.
7. A compound of formula II :
Formula II wherein
R and R are independently selected from halogen or alkyl; R8 is selected from halogen, hydroxyl or -OSO2R9 wherein R is alkyl or aryl; and x is 2, 3, 4, 5 or 6.
EP06739229A 2005-03-23 2006-03-22 Improved process for preparing insecticidal (disubstitutedpropenyl) phenylalkyl substituted dihydrobenzofurans Withdrawn EP1863783A4 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US66442705P 2005-03-23 2005-03-23
PCT/US2006/010350 WO2006102387A1 (en) 2005-03-23 2006-03-22 Improved process for preparing insecticidal (disubstitutedpropenyl) phenylalkyl substituted dihydrobenzofurans

Publications (2)

Publication Number Publication Date
EP1863783A1 EP1863783A1 (en) 2007-12-12
EP1863783A4 true EP1863783A4 (en) 2008-06-18

Family

ID=37024160

Family Applications (1)

Application Number Title Priority Date Filing Date
EP06739229A Withdrawn EP1863783A4 (en) 2005-03-23 2006-03-22 Improved process for preparing insecticidal (disubstitutedpropenyl) phenylalkyl substituted dihydrobenzofurans

Country Status (6)

Country Link
EP (1) EP1863783A4 (en)
JP (1) JP2008534507A (en)
CN (1) CN101146788A (en)
IL (1) IL186017A0 (en)
TW (1) TW200716585A (en)
WO (1) WO2006102387A1 (en)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1986000904A1 (en) * 1984-07-18 1986-02-13 Nitrokémia Ipartelepek Etherified 2-hydroxy-ethyl-phosphonic acid derivatives and plant growth regulating agents containing same as active ingredient
US4960884A (en) * 1989-03-02 1990-10-02 Fmc Corporation Pesticidal 2-fluoroethyl ethers
JPH05125024A (en) * 1991-11-05 1993-05-21 Yamanouchi Pharmaceut Co Ltd New aryloxyalkylamine derivative or its salt
EP0976747A2 (en) * 1998-07-27 2000-02-02 Eli Lilly And Company Use of 5HT-1F receptor antagonists for treating anxiety disorders
WO2004098283A2 (en) * 2003-04-30 2004-11-18 Fmc Corporation Insecticidal (dihalopropenyl) phenylalkyl substituted dihydrobenzofuran and dihydrobenzopyran derivatives
WO2006089024A1 (en) * 2005-02-17 2006-08-24 Bayer Cropscience Ag Improved process for preparing (disubstitutedpropenyl) phenylalkyl substituted dihydrobenzofurans
WO2006088963A1 (en) * 2005-02-17 2006-08-24 Bayer Cropscience Ag Improved process for preparing (disubstitutedpropenyl) phenylalkyl substituted dihydrobenzofurans

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1986000904A1 (en) * 1984-07-18 1986-02-13 Nitrokémia Ipartelepek Etherified 2-hydroxy-ethyl-phosphonic acid derivatives and plant growth regulating agents containing same as active ingredient
US4960884A (en) * 1989-03-02 1990-10-02 Fmc Corporation Pesticidal 2-fluoroethyl ethers
JPH05125024A (en) * 1991-11-05 1993-05-21 Yamanouchi Pharmaceut Co Ltd New aryloxyalkylamine derivative or its salt
EP0976747A2 (en) * 1998-07-27 2000-02-02 Eli Lilly And Company Use of 5HT-1F receptor antagonists for treating anxiety disorders
WO2004098283A2 (en) * 2003-04-30 2004-11-18 Fmc Corporation Insecticidal (dihalopropenyl) phenylalkyl substituted dihydrobenzofuran and dihydrobenzopyran derivatives
WO2006089024A1 (en) * 2005-02-17 2006-08-24 Bayer Cropscience Ag Improved process for preparing (disubstitutedpropenyl) phenylalkyl substituted dihydrobenzofurans
WO2006088963A1 (en) * 2005-02-17 2006-08-24 Bayer Cropscience Ag Improved process for preparing (disubstitutedpropenyl) phenylalkyl substituted dihydrobenzofurans

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
ATKINSON, PETER J. ET AL: "3,4-Dihydro-2H-benzoxazinones are 5-HT1A receptor antagonists with potent 5-HT reuptake inhibitory activity", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS , 15(3), 737-741 CODEN: BMCLE8; ISSN: 0960-894X, 23 December 2004 (2004-12-23), XP004739690 *
KOSSAKOWSKI J ET AL: "SYNTHESIS AND STRUCTURAL CHARACTERIZATION OF AMINOALKANOL DERIVATIVES OF 2,3-DIHYDRO-2,2-DIMETHYL-7-BENZOFURANOL WITH AN EXPECTED BETA-ADRENOLYTIC AND/OR ANXIOLYTIC ACTIVITY", ZEITSCHRIFT FUER NATURFORSCHUNG. TEIL B, ANORGANISCHE CHEMIE,ORGANISCHE CHEMIE, VERLAG DER ZEITSCHRIFT FUER NATURFORSCHUNG, TUEBINGEN, DE, vol. 57, no. 3, 1 January 2002 (2002-01-01), pages 286 - 294, XP009022032, ISSN: 0340-5087 *
See also references of WO2006102387A1 *

Also Published As

Publication number Publication date
WO2006102387A1 (en) 2006-09-28
CN101146788A (en) 2008-03-19
IL186017A0 (en) 2008-01-20
TW200716585A (en) 2007-05-01
EP1863783A1 (en) 2007-12-12
JP2008534507A (en) 2008-08-28

Similar Documents

Publication Publication Date Title
EP1853614A1 (en) Improved process for preparing (disubstitutedpropenyl) phenylalkyl substituted dihydrobenzofurans
JP5721720B2 (en) Method for producing methylene disulfonate compound
JP2009507867A (en) Process for producing 5-fluoro-1,3-dialkyl-1H-pyrazole-4-carbonyl fluoride
JP4571374B2 (en) Process for producing 7-substituted 3-alkyl-3H-isobenzofuran-1-one derivatives
JP5008404B2 (en) Method for producing methylene disulfonate compound
WO2006089024A1 (en) Improved process for preparing (disubstitutedpropenyl) phenylalkyl substituted dihydrobenzofurans
EP1863783A1 (en) Improved process for preparing insecticidal (disubstitutedpropenyl) phenylalkyl substituted dihydrobenzofurans
JP2008074804A (en) Method for producing silane compound having isocyanate group
JP2006188449A (en) Method for producing cyclic disulfonic acid ester
WO2019208043A1 (en) Method for producing n-unprotected imine compound
JP2003335735A (en) Method for producing perfluoroisopropylanilines
JP4963970B2 (en) Method for producing methylene disulfonate compound
KR101918520B1 (en) A process for preparing laurolactam
CA3000198C (en) Alkylation of picolinamides with substituted chloroacylals utilizing a crown ether catalyst
JP6853709B2 (en) Aromatic compounds and methods for producing them
JP2010260805A (en) Method of producing isothiazole derivative
JP5268264B2 (en) Method for producing alkanedisulfonyl halide
JP6853086B2 (en) Aromatic compounds and methods for producing them
JPH08239338A (en) Method of synthesizing methyl-1,1-dichloromethyl ether ethyl-1,1-dichloro-methyl ether
JPH10298156A (en) Production of substituted halomethylphenylcarbamic acid esters
JP2010222346A (en) Hexathiaadamantane compound and method for producing the same
EP1902023A2 (en) Improved process for preparing insecticidal (disubstitutedpropenyl) phenylalkyl substituted heterocycles
JP2007277201A (en) Aromatic dihydroxy compound and its production method
WO2007039127A1 (en) A process for the preparation and purification of bicalutamide
JP2007186436A (en) Method for producing 5-halo-2-alkylthio-benzaldehyde

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20071023

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU LV MC NL PL PT RO SE SI SK TR

A4 Supplementary search report drawn up and despatched

Effective date: 20080520

DAX Request for extension of the european patent (deleted)
17Q First examination report despatched

Effective date: 20080903

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20090114