WO2006102387A1 - Improved process for preparing insecticidal (disubstitutedpropenyl) phenylalkyl substituted dihydrobenzofurans - Google Patents

Improved process for preparing insecticidal (disubstitutedpropenyl) phenylalkyl substituted dihydrobenzofurans Download PDF

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Publication number
WO2006102387A1
WO2006102387A1 PCT/US2006/010350 US2006010350W WO2006102387A1 WO 2006102387 A1 WO2006102387 A1 WO 2006102387A1 US 2006010350 W US2006010350 W US 2006010350W WO 2006102387 A1 WO2006102387 A1 WO 2006102387A1
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formula
compound
disubstitutedpropenyl
halogen
substituted
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PCT/US2006/010350
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French (fr)
Inventor
Jaidev S. Goudar
Charles E. Hatch, Iii
Guozhi Wang
Russell Patera
Craig A. Polsz
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Bayer Cropscience Ag
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Priority to EP06739229A priority Critical patent/EP1863783A4/en
Priority to JP2008503120A priority patent/JP2008534507A/en
Publication of WO2006102387A1 publication Critical patent/WO2006102387A1/en
Priority to IL186017A priority patent/IL186017A0/en

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    • 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

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Furan Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (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:
Figure imgf000002_0001
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:
Figure imgf000003_0001
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:
Figure imgf000003_0002
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):
Figure imgf000004_0001
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)
Figure imgf000004_0002
Formula II
wherein
R 5 R R and x are as defined above; and
b) reacting a compound of formula (C):
Figure imgf000005_0001
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:
Figure imgf000006_0001
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):
Figure imgf000006_0002
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:
Figure imgf000007_0001
Formula II wherein
R5, R6 R8 and x are as defined above; and
reacting a compound of formula (CJ:
Figure imgf000007_0002
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:
Figure imgf000008_0001
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
Figure imgf000009_0001
wherein R5 and R6 are alkyl wherein R7 and R8 are halogen π
are alkyl
Figure imgf000009_0002
Figure imgf000009_0003
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:
Figure imgf000011_0001
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):
Figure imgf000011_0002
Formula (A)
wherein R5 and R6 are as defined above;
with a compound of formula (B):
Figure imgf000011_0003
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:
Figure imgf000012_0001
Formula II
wherein R , R R and x are as defined above; and
reacting a compound of formula (C):
Figure imgf000012_0002
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 :
Figure imgf000013_0001
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.
PCT/US2006/010350 2005-03-23 2006-03-22 Improved process for preparing insecticidal (disubstitutedpropenyl) phenylalkyl substituted dihydrobenzofurans WO2006102387A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP06739229A EP1863783A4 (en) 2005-03-23 2006-03-22 Improved process for preparing insecticidal (disubstitutedpropenyl) phenylalkyl substituted dihydrobenzofurans
JP2008503120A JP2008534507A (en) 2005-03-23 2006-03-22 Improved process for preparing (disubstituted propenyl) phenylalkyl substituted dihydrobenzofurans having insecticidal activity
IL186017A IL186017A0 (en) 2005-03-23 2007-09-18 Improved process for preparing insecticidal (disubtitutedpropenyl) phenylalkyl substituted dihydrobenzofurans

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US66442705P 2005-03-23 2005-03-23
US60/664,427 2005-03-23

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Citations (1)

* 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

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
JP2003527305A (en) * 1998-07-27 2003-09-16 イーライ・リリー・アンド・カンパニー Anxiety treatment
CN1780818A (en) * 2003-04-30 2006-05-31 Fmc有限公司 Derivados ciclicos fenil-substituidos
BRPI0608084A2 (en) * 2005-02-17 2009-11-10 Bayer Cropscience Ag improved process for preparing phenylalkyl-substituted dihydrobenzofurans (disubstituted propenyl)
WO2006088963A1 (en) * 2005-02-17 2006-08-24 Bayer Cropscience Ag Improved process for preparing (disubstitutedpropenyl) phenylalkyl substituted dihydrobenzofurans

Patent Citations (1)

* 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

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE CA [online] 1986, BALINT S. ET AL.: "Etherified 2-hydroxyethylphosphonic acid derivatives and plant growth regulating agents containing them as active ingredient", XP003001987, Database accession no. (105:134144) *
See also references of EP1863783A4 *

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EP1863783A1 (en) 2007-12-12
JP2008534507A (en) 2008-08-28

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