Dimethylformamide → Ethyl 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxybutyrate

HRID 618404Notes

Reaction equation

HRID 618404 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[CH:17]([CH3:24])[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[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[O:15][CH:18]([CH2:17][CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 95424Butanoic acid, 3-bromo-, ethyl esterHCID 113467384-(3,3-Dichloro-2-propenyloxy)-2,6-dichlorophenol

Product 1

HCID 86754493Ethyl 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxybutyrateYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A reaction vessel was charged with 2.02 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol, 1.56 g of ethyl 3-bromobutyrate, 1.11 g of potassium carbonate and 20 ml of N,N-dimethylformamide. After stirring at room temperature for 12 hours, the reaction mixture was poured into water and extracted twice with 50 ml of diethyl ether. The 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 2.54 g of ethyl 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxybutyrate (90% yield).

Workup

  1. extractionextracted twice with 50 ml of diethyl ether
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto give a crude product

Sources & evidence

ORD record
ord-8f16dce439dc48a8ae50c1983d7baeef
Source dataset
uspto-grants-1999_09
Patent number
US05952386

Reaction notes

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