Thionyl Chloride → 2-[4-(5-Chloro-3-fluoropyridin-2-yloxy)phenoxy]propionyl chloride

HRID 235559Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([F:21])[C:5]([O:8][C:9]2[CH:20]=[CH:19][C:12]([O:13][CH:14]([CH3:18])[C:15](O)=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.S(Cl)([Cl:24])=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([F:21])[C:5]([O:8][C:9]2[CH:20]=[CH:19][C:12]([O:13][CH:14]([CH3:18])[C:15]([Cl:24])=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

63.6 g of 2-[4-(5-chloro-3-fluoropyridin-2-yloxy)phenoxy]propionic acid are dissolved in 700 ml of toluene, then 200 ml of toluene are removed from this solution by distillation. After cooling to 90° C., 25 ml (0.34 mole) of thionyl chloride are added dropwise and the solution is stirred for 14 hours at this temperature. The reaction mixture is then concentrated to a volume of 200 ml and the resultant solution of 2-[4-(5-chloro-3-fluoropyridin-2-yloxy)phenoxy]propionyl chloride in toluene is used direct for the following reaction step.

Workup

custom200 ml of toluene are removed from this solution by distillation
concentrationThe reaction mixture is then concentrated to a volume of 200 ml
customthe resultant solution of 2-[4-(5-chloro-3-fluoropyridin-2-yloxy)phenoxy]propionyl chloride in toluene is used direct for the following reaction step

Sources & evidence

ORD record: ord-80d1fc25c29e4d78a750e316acaeaab6
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04640703

Reaction notes

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