Sodium Iodide → 3-Chloro-5-(3,3-dichloroprop-2-enyloxy)-1-iodo-2-[3-(5-trifluoromethylpyrid-2-yloxy)propyloxy]benzene

HRID 497053Notes

Reaction equation

HRID 497053 reaction equation
[Cl:1][C:2]1[C:3]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][N:16]=2)=[C:4]([I:9])[CH:5]=[C:6]([OH:8])[CH:7]=1.[Cl:25][C:26]([Cl:30])=[CH:27][CH2:28]Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O>[Cl:1][C:2]1[C:3]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:22])[F:23])=[CH:17][N:16]=2)=[C:4]([I:9])[CH:5]=[C:6]([O:8][CH2:28][CH:27]=[C:26]([Cl:30])[Cl:25])[CH:7]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 173781,1,3-TrichloropropeneHCID 223186173-Chloro-5-hydroxy-1-iodo-2-[3-(5-trifluoromethylpyrid-2-yloxy)propyloxy]-benzene

Product 1

HCID 223186113-Chloro-5-(3,3-dichloroprop-2-enyloxy)-1-iodo-2-[3-(5-trifluoromethylpyrid-2-yloxy)propyloxy]benzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2.23 g of 3-chloro-5-hydroxy-1-iodo-2-[3-(5-trifluoromethylpyrid-2-yloxy)propyloxy]-benzene were dissolved in 22 ml of acetone, and 0.79 g of 1,1,3-trichloropropene, 1.3 g of potassium carbonate and 0.27 g of sodium iodide were added. The mixture was stirred at room temperature for 20 hours (monitored by TLC). The reaction mixture was then concentrated using a rotary evaporator, and the resulting crude product was subjected to chromatographic purification. Yield: 2.62 g (95%)

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customa rotary evaporator
  3. customthe resulting crude product was subjected to chromatographic purification

Sources & evidence

ORD record
ord-52fdcb206fbf4b77bb12b156b23c9937
Source dataset
uspto-grants-2005_09
Patent number
US06949551B2

Reaction notes

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