Potassium Carbonate → 3,5-Dichloro-4-(3-(4-trifluoromethylphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

HRID 363070Notes

Reaction equation

HRID 363070 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:14][CH2:15][CH:16]=[C:17]([Cl:19])[Cl:18])[CH:5]=[C:6]([Cl:13])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11]Br.[F:20][C:21]([F:30])([F:29])[C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([O:14][CH2:15][CH:16]=[C:17]([Cl:19])[Cl:18])[CH:5]=[C:6]([Cl:13])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][O:28][C:25]1[CH:26]=[CH:27][C:22]([C:21]([F:20])([F:29])[F:30])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 678744-(Trifluoromethyl)phenolHCID 108840691-[4-(3,3-Dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]-3-bromopropane

Product 1

HCID 541871753,5-Dichloro-4-(3-(4-trifluoromethylphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzeneYield 72.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.56 g of 3,5-dichloro-4-(3-bromopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene, 0.22 g of 4-trifluoromethylphenol, 0.21 g of potassium carbonate and 20 ml of N,N-dimethylformamide was stirred at room temperature. After stirring for 7 hours, the reaction mixture was poured into ice-water, and extracted twice with 50 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.48 g of 3,5-dichloro-4-(3-(4-trifluoromethylphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene (71% yield), nD24.4 1.5390.

Workup

  1. stirringAfter stirring for 7 hours
  2. extractionextracted twice with 50 ml of diethyl ether
  3. washThe combined ether layer was washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customto obtain a crude product

Sources & evidence

ORD record
ord-7118dc9b48b3488d8679d8a79350e22b
Source dataset
uspto-grants-1999_02
Patent number
US05872137

Reaction notes

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