Dichloromethane → HCID 86750235, compound

HRID 234841Notes

Reaction equation

HRID 234841 reaction equation
C(CO[C:6]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[C:18]([Cl:26])[CH:17]=2)=[CH:11][C:7]=1[C:8](O)=[O:9])(O)=O.[C:27](Cl)(=[O:31])[C:28]([Cl:30])=[O:29].C(Cl)[Cl:34]>CN(C)C=O.C1(C)C=CC=CC=1>[Cl:30][C:28]([CH2:27][O:31][C:6]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[C:18]([Cl:26])[CH:17]=2)=[CH:11][C:7]=1[C:8]([Cl:34])=[O:9])=[O:29]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 86750236HCID 86750236, compound

Product 1

HCID 86750235HCID 86750235, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
-8 °C

Procedure

A mixture of 2-(carboxymethoxy)-5-[(2-chloro -α,α,α-trifluoro-p-tolyl)oxy]benzoic acid (16.0 g, 40.95 mmol) in methylene chloride is cooled to -8° C., treated with oxalyl chloride (20.8 g, 163.8 mmol) and four drops of N,N-dimethylformamide, stirred for several minutes and concentrated in vacuo to obtain a solid. The solid is dissolved in toluene and the resultant organic solution is concentrated in vacuo to give the title product as an off-white solid (16.7 g, 95.4%).

Workup

  1. concentrationconcentrated in vacuo
  2. customto obtain a solid
  3. concentrationthe resultant organic solution is concentrated in vacuo

Sources & evidence

ORD record
ord-f1bfc029914446da9ac40b33fe51eb30
Source dataset
uspto-grants-1997_01
Patent number
US05596124

Reaction notes

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