Dimethylformamide → (R)-2-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy]propionic acid chloride

HRID 1248087Notes

Reaction equation

HRID 1248087 reaction equation
[Cl:1][C:2]1[C:3]([O:12][C:13]2[CH:24]=[CH:23][C:16]([O:17][C@H:18]([CH3:22])[C:19](O)=[O:20])=[CH:15][CH:14]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.S(Cl)([Cl:27])=O.CN(C=O)C>CCOCC>[Cl:1][C:2]1[C:3]([O:12][C:13]2[CH:24]=[CH:23][C:16]([O:17][C@H:18]([CH3:22])[C:19]([Cl:27])=[O:20])=[CH:15][CH:14]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 448979Haloxyfop-P

Product 1

HCID 13389071(R)-2-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy]propionic acid chloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1.06 g (2.94 mmol) of (R)-2-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy]propionic acid in 5 ml of dry ether under a nitrogen atmosphere and cooled to 0° is added 400 μl (5.50 mmol, 0.66 g) of thionyl chloride and 50 μl of DMF. After 5 hours at 0°, the reaction is stirred at RT overnight. The ether solution of acid chloride is then removed from the oily residue, and the ether and excess thionyl chloride are removed by rotoevaporation to give (R)-2-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy]propionic acid chloride.

Workup

  1. customThe ether solution of acid chloride is then removed from the oily residue
  2. customthe ether and excess thionyl chloride are removed by rotoevaporation

Sources & evidence

ORD record
ord-f1b945c56d2f4772a9a09430f198497e
Source dataset
uspto-grants-1985_06
Patent number
US04522647

Reaction notes

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