1,3-Dibromopropane → 1-[4-(3,3-Dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]-3-bromopropane

HRID 1280233Notes

Reaction equation

HRID 1280233 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH:10]=[C:11]([Cl:13])[Cl:12])[CH:5]=[C:4]([Cl:14])[C:3]=1[OH:15].[Br:16][CH2:17][CH2:18][CH2:19]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:16][CH2:17][CH2:18][CH2:19][O:15][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([O:8][CH2:9][CH:10]=[C:11]([Cl:13])[Cl:12])=[CH:5][C:4]=1[Cl:14]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 113467384-(3,3-Dichloro-2-propenyloxy)-2,6-dichlorophenol

Product 1

HCID 108840691-[4-(3,3-Dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]-3-bromopropaneYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

First, 10.0 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol, 14.0 g of 1,3-dibromopropane, and 50 ml of N,N-dimethylformamide were placed in a reaction vessel, to which 5.3 g of potassium carbonate was added. After stirring at room temperature for 12 hours, the reaction mixture was filtered. The filtrate was poured into diluted hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer was washed twice with water, dried over anhydrous magnesium sulfate, and concentrated to give a crude product. This crude product was subjected to silica gel chromatography, which afforded 6.1 g (yield, 43%) of 1-(3-bromopropyloxy)-2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)benzene.

Workup

  1. additionwas added
  2. filtrationthe reaction mixture was filtered
  3. additionThe filtrate was poured into diluted hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed twice with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customto give a crude product

Sources & evidence

ORD record
ord-94efcba1cc7d4ce0a1f9c18dd5fc95b0
Source dataset
uspto-grants-2002_09
Patent number
US06448444B1

Reaction notes

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