# US 4,393,213 A · Process for producing 6-phenoxypicolinic aldehydes

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- Number: US 4,393,213 A
- Document ID: US4393213A
- Status: Granted
- Kind: A
- Application number: 06/315,228
- Filed: 1981-10-26
- Granted: 1983-07-12
- Earliest claimed: 1981-01-14
- Assignees: Nissan Chemical Industries, Ltd.
- Inventors: Kiyomi Ozawa; Shigeru Ishii
- Web page: https://patentgrep.com/patent/US4393213A

## CPC

- C07D 213/643: 2-Phenoxypyridines; Derivatives thereof
- A01N 43/40: six-membered rings
- A01N 53/00: Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
- C07D 213/647: and having in the molecule an acyl radical containing a saturated three-membered ring, e.g. chrysanthemumic acid esters
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS

## Abstract

A process for producing 6-phenoxypicolinic aldehydes, which comprises reacting a 2-halogeno-6-phenoxypyridine represented by the general formula I: ##STR1## where X is a halogen atom, Y is independently an alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms substituted by a halogen atom, an alkylthio group of 1 to 4 carbon atoms, a trifluoromethyl group, a fluorine atom or a chlorine atom, Z is a hydrogen atom or a fluorine atom, and n is an integer of 0 to 2, with magnesium metal, and then with a formylating reagent. These compounds are used as intermediates for the synthesis of insecticides.

## Claims

### Claim 1

A process for producing 6-phenoxypicolinic aldehydes, which comprises reacting a 2-halogeno-6-phenoxypyridine represented by the general formula I:
where X is a halogen atom, Y is independently an alkyl group of 1 to 4 carbon atoms, an alkoxyl group of 1 to 4 carbon atoms, an alkoxyl group of 1 to 4 carbon atoms substituted by a halogen atom, an alkylthio group of 1 to 4 carbon atoms, a trifluoromethyl group, a fluorine atom or a chlorine atom, Z is a hydrogen atom or a fluorine atom, said magnesium metal being in an amount of from 1 to 2 equivalents to said 2-halogeno-6-phenoxypyridine, and n is an integer of 0 to 2, with

### Claim 2 (depends on 1)

A process according to claim 1, wherein the halogen atom represented by

### Claim 3 (depends on 1)

A process according to claim 1, wherein said magnesium metal is used in an amount of from 1 to 1.2 equivalents to said

### Claim 4 (depends on 1)

A process according to claim 1, wherein said formylating reagent is a

### Claim 5 (depends on 4)

A process according to claim 4, wherein said formamide is dimethylformamide or N-methylformanilide, and said ester is orthoformic

### Claim 6 (depends on 1, 4)

A process according to claim 1, 4, or 5, wherein said formylating reagent is added in an amount of 1 equivalent to the Grignard compound.

### Claim 7 (depends on 1)

A process according to claim 1, wherein a solvent is used in said

### Claim 8 (depends on 7)

A process according to claim 7, wherein said solvent is a polar inert

### Claim 9 (depends on 8)

A process according to claim 8, wherein said polar inert organic solvent

### Claim 10 (depends on 1)

A process according to claim 1, wherein a reaction initiator or a

### Claim 11 (depends on 1, 2, 3, 4, 5, 10)

A process according to any one of claims 1, 2, 3, 4, 5 or 10, wherein said reaction with magnesium metal is carried out in the presence of

### Claim 12 (depends on 6)

A process according to claim 6, wherein said reaction with magnesium

### Claim 16 (depends on 12)

A process according to claim 12, wherein X is a chlorine atom.