p-Chlorothiophenol → HCID 54339509, compound

HRID 363079Notes

Reaction equation

HRID 363079 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.Br[CH2:10][CH2:11][CH2:12][O:13][C:14]1[C:19]([Cl:20])=[CH:18][C:17]([O:21][CH2:22][CH:23]=[C:24]([Cl:26])[Cl:25])=[CH:16][C:15]=1[Cl:27].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:10][CH2:11][CH2:12][O:13][C:14]2[C:15]([Cl:27])=[CH:16][C:17]([O:21][CH2:22][CH:23]=[C:24]([Cl:26])[Cl:25])=[CH:18][C:19]=2[Cl:20])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7815p-ChlorothiophenolHCID 11430Potassium CarbonateHCID 108840691-[4-(3,3-Dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]-3-bromopropane

Product 1

HCID 54339509HCID 54339509, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.47 g of 4-chlorothiophenol, 1.33 g of 1-(3-bromopropyloxy)-2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)benzene, 0.49 g of potassium carbonate and 20 ml of N,N-dimethylformamide was stirred at room temperature for 24 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 1.24 g of 1-(3-(4-chlorophenylthio) propyloxy)-2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)benzene (81% yield), nD26.0 1.6035.

Workup

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

Sources & evidence

ORD record
ord-da4860ab00af4b76afa7e756d6aa2d5d
Source dataset
uspto-grants-1999_02
Patent number
US05872137

Reaction notes

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