Potassium Carbonate → 3-Chloro-4-[3-(4-trifluoromethylphenoxy) propyloxy]-5-methyl-1-(3,3-dichloro-2-propenyloxy)benzene

HRID 363086Notes

Reaction equation

HRID 363086 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1.BrCCCOC1C=CC(OC(F)(F)F)=CC=1.C(=O)([O-])[O-].[K+].[K+].[Cl:38][C:39]1[CH:44]=[C:43]([O:45][CH2:46][CH:47]=[C:48]([Cl:50])[Cl:49])[CH:42]=[C:41]([CH3:51])[C:40]=1[OH:52]>CN(C)C=O.C(OCC)C>[Cl:38][C:39]1[CH:44]=[C:43]([O:45][CH2:46][CH:47]=[C:48]([Cl:49])[Cl:50])[CH:42]=[C:41]([CH3:51])[C:40]=1[O:52][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11781023Benzene, 1-(3-bromopropoxy)-4-(trifluoromethyl)-HCID 136722751-(3-Bromopropoxy)-4-(trifluoromethoxy)benzeneHCID 185046952-Chloro-6-methyl-4-(3,3-dichloro-2-propenyloxy)phenol

Product 1

HCID 538030523-Chloro-4-[3-(4-trifluoromethylphenoxy) propyloxy]-5-methyl-1-(3,3-dichloro-2-propenyloxy)benzeneYield 94.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

First, 0.35 g of 1-(3-bromopropyloxy)-4-trifluoromethylbenzene (prepared in the same manner as described above for 1-(3-bromopropyloxy)-4-trifluoromethoxybenzene) and 0.2 g of potassium carbonate were dissolved in 100 ml of N,N-dimethylformamide, to which 0.3 g of 2-chloro-6-methyl-4-(3,3-dichloro-2-propenyloxy)phenol was added, and the mixture was stirred at room temperature for 24 hours. The reaction mixture was mixed with 200 ml of diethyl ether, 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 0.50 g of 3-chloro-4-[3-(4-trifluoromethylphenoxy) propyloxy]-5-methyl-1-(3,3-dichloro-2-propenyloxy)benzene (94% yield), nD23.0 1.5330.

Workup

  1. additionwas added
  2. washwashed with water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto obtain a crude product

Sources & evidence

ORD record
ord-ea71162892f44dcabd4cc1a971eff7e4
Source dataset
uspto-grants-1999_02
Patent number
US05872137

Reaction notes

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