Diphenyl Ether → Methyl-5-(2-chloro-4-cyano-6-fluoro-phenoxy)-2-nitro-benzoate

HRID 280728Notes

Reaction equation

HRID 280728 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:11])[C:9]=1F)[C:5]#[N:6].C1(OC2C=CC=CC=2)C=CC=CC=1.[K].[CH3:26][O:27][C:28](=[O:39])[C:29]1[CH:34]=[C:33]([OH:35])[CH:32]=[CH:31][C:30]=1[N+:36]([O-:38])=[O:37]>CN1CCCC1=O>[CH3:26][O:27][C:28](=[O:39])[C:29]1[CH:34]=[C:33]([O:35][C:9]2[C:8]([F:11])=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=2[Cl:1])[CH:32]=[CH:31][C:30]=1[N+:36]([O-:38])=[O:37]

Participants

6

Reactant 4

HCID 7583Diphenyl EtherHCID 5462222PotassiumHCID 12922678Methyl 5-hydroxy-2-nitrobenzoateHCID 136434703-Chloro-4,5-difluorobenzonitrile

Product 1

HCID 23035893Methyl-5-(2-chloro-4-cyano-6-fluoro-phenoxy)-2-nitro-benzoate

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The product 3-chloro-4,5-difluorobenzonitrile, prepared for example as set forth in Example 3, above, is a useful intermediate for the preparation of various end products especially for the preparation of diphenyl ether herbicides. Thus, for example, this compound may be further reacted with the potassium salt of methyl-5-hydroxy-2-nitrobenzoate in a solvent, such as N-methyl-2-pyrrolidone at a temperature of about 120° to 180° Celsius to form methyl-5-(2-chloro-4-cyano-6-fluoro-phenoxy)-2-nitro-benzoate. The ester may be hydrolyzed in a conventional manner to the corresponding carboxylic acid.

Workup

  1. customfor the preparation of various end products

Sources & evidence

ORD record
ord-9654b819cb6344e78c270f6b659d72c2
Source dataset
uspto-grants-1986_05
Patent number
US04590315

Reaction notes

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