2,4,6-Trichlorophenol → HCID 86672958, compound

HRID 1023278Notes

Reaction equation

HRID 1023278 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:12]([OH:14])=[O:13])[C:9]([OH:11])=[O:10].[C:15]([Cl:20])(=O)[C:16](Cl)=O.[Cl:21][C:22]1[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([Cl:29])[C:23]=1O>ClCCl.CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:9]([O:11][C:16]1[C:15]([Cl:20])=[CH:27][C:22]([Cl:21])=[CH:23][C:24]=1[Cl:29])=[O:10])[C:12]([O:14][C:27]1[C:22]([Cl:21])=[CH:23][C:24]([Cl:29])=[CH:25][C:26]=1[Cl:28])=[O:13]

Participants

6

Reactant 3

HCID 69142,4,6-TrichlorophenolHCID 65578Oxalyl chlorideHCID 57249691HCID 57249691, compound

Product 1

HCID 86672958HCID 86672958, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-fluorophenyl)propanedioic acid (0.60 g, 3 mmol, prepared by the method described in Eur. J. Biochem. 1992, 210, 475) in dichloromethane (5 mL) was added oxalyl chloride (0.65 mL, 7.5 mmol) and one drop of N,N-dimethylformamide. The reaction mixture was stirred for 1 h at room temperature. 2,4,6-Trichlorophenol (1.47 g, 7.5 mmol) was then added, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and the crude residue was triturated with a small amount of cold methanol to yield the title compound as a white solid (1.1 g).

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe crude residue was triturated with a small amount of cold methanol

Sources & evidence

ORD record
ord-d4c51b2259ea4c6eba1a5ed31430a03f
Source dataset
uspto-grants-2014_05
Patent number
US08722690B2

Reaction notes

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