Potassium Iodide → 2-{3-[2,6-Dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propyl}-2-(4-fluoro-phenyl)-[1,3]dioxolane

HRID 1869148Notes

Reaction equation

HRID 1869148 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]1([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[O:9][CH2:8][CH2:7][O:6]1.[Cl:17][C:18]1[CH:23]=[C:22]([O:24][CH2:25][CH:26]=[C:27]([Cl:29])[Cl:28])[CH:21]=[C:20]([Cl:30])[C:19]=1[OH:31].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[Cl:17][C:18]1[CH:23]=[C:22]([O:24][CH2:25][CH:26]=[C:27]([Cl:29])[Cl:28])[CH:21]=[C:20]([Cl:30])[C:19]=1[O:31][CH2:2][CH2:3][CH2:4][C:5]1([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[O:9][CH2:8][CH2:7][O:6]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 27237782-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolaneHCID 113467384-(3,3-Dichloro-2-propenyloxy)-2,6-dichlorophenol

Product 1

HCID 866130872-{3-[2,6-Dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propyl}-2-(4-fluoro-phenyl)-[1,3]dioxolane

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

2.0 g of 2-(3-chloro-propyl)-2-(4-fluoro-phenyl)-[1,3]dioxolane are added to a suspension of 2.36 g of 2,6-dichloro-4-(3,3-dichloro-allyloxy)-phenol, 1.7 g of potassium carbonate and 120 mg of potassium iodide in 50 ml of acetone. The mixture is then stirred for 48 hours at 60° C. The reaction mixture is concentrated and the residue is taken up in water and extracted with ethyl acetate. After concentration of the organic phase and purification over silica gel, 2-{3-[2,6-dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propyl}-2-(4-fluoro-phenyl)-[1,3]dioxolane is obtained.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. extractionextracted with ethyl acetate
  3. customAfter concentration of the organic phase and purification over silica gel

Sources & evidence

ORD record
ord-83161661a247422c8e54442bf3390b6b
Source dataset
uspto-grants-2009_12
Patent number
US07638514B2

Reaction notes

Loading…