Water → 1-[4-(3,3-Dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]-4-bromobutane

HRID 369690Notes

Reaction equation

HRID 369690 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5]Br.C(=O)([O-])[O-].[K+].[K+].[Cl:13][C:14]1[CH:19]=[C:18]([O:20][CH2:21][CH:22]=[C:23]([Cl:25])[Cl:24])[CH:17]=[C:16]([Cl:26])[C:15]=1[OH:27].O>CN(C)C=O>[Cl:13][C:14]1[CH:19]=[C:18]([O:20][CH2:21][CH:22]=[C:23]([Cl:25])[Cl:24])[CH:17]=[C:16]([Cl:26])[C:15]=1[O:27][CH2:5][CH2:4][CH2:3][CH2:2][Br:1]

Participants

6

Reactant 4

HCID 962WaterHCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 113467384-(3,3-Dichloro-2-propenyloxy)-2,6-dichlorophenol

Product 1

HCID 222571451-[4-(3,3-Dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]-4-bromobutaneYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A reaction vessel was charged with 22.67 g of 1,4-dibromobutane, 11.06 g of potassium carbonate and 200 ml of N,N-dimethylformamide, to which a solution of 20.16 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol dissolved in 80 ml of N,N-dimethylformamide was slowly added dropwise. After stirring at room temperature for 24 hours, the reaction mixture was poured into water and extracted twice with 300 ml of diethyl ether. The diethyl ether layers were combined, washed with water, dried over anhydrous magnesium sulfate and then concentrated to give a crude product. The crude product was subjected to silica gel chromatography, which afforded 21.77 g of 3,5-dichloro-4-(4-bromobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene (yield, 74%), nD25.0 1.5666.

Workup

  1. additionwas slowly added dropwise
  2. extractionextracted twice with 300 ml of diethyl ether
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customto give a crude product

Sources & evidence

ORD record
ord-0284182e24304690b7c489b639fcab6f
Source dataset
uspto-grants-2000_10
Patent number
US06140274

Reaction notes

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