Potassium Carbonate → 2,5-Dichloro-4-(3-bromo-5-trifluoromethyl-2-pyridyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

HRID 1940239Notes

Reaction equation

HRID 1940239 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:14]([Br:15])=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][N:10]=2)[C:5]([Cl:20])=[CH:4][C:3]=1[OH:21].C(=O)([O-])[O-].[K+].[K+].[Cl:28][C:29]([Cl:33])=[CH:30][CH2:31]Cl>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:14]([Br:15])=[CH:13][C:12]([C:16]([F:17])([F:19])[F:18])=[CH:11][N:10]=2)[C:5]([Cl:20])=[CH:4][C:3]=1[O:21][CH2:31][CH:30]=[C:29]([Cl:33])[Cl:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 173781,1,3-TrichloropropeneHCID 214663082,5-Dichloro-4-(3-bromo-5-trifluoromethyl-2-pyridyloxy)phenol

Product 1

HCID 214663982,5-Dichloro-4-(3-bromo-5-trifluoromethyl-2-pyridyloxy)-1-(3,3-dichloro-2-propenyloxy)benzeneYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 0.77 g of 2,5-dichloro-4-(3-bromo-5-trifluoromethyl-2-pyridyloxy)phenol, 0.29 g of potassium carbonate and 20 ml of N,N-dimethylformamide, a solution prepared by dissolving 0.31 g of 1,1,3-trichloropropene in 5 ml of N,N-dimethylformamide was added dropwise at room temperature with stirring. After stirring at room temperature for 10 hours, the reaction solution was poured into ice-water, and extracted twice with 50 ml of ethyl acetate. Then, the ethyl acetate layers were combined, washed with water, dried over anhydrous magnesium sulfate and then concentrated to give a crude product. This crude product was subjected to silica gel chromatography to give 0.81 g of 2,5-dichloro-4-(3-bromo-5-trifluoromethyl-2-pyridyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene, yield 83%; m.p., 95.4° C.

Workup

  1. customa solution prepared
  2. additionwas added dropwise at room temperature
  3. stirringAfter stirring at room temperature for 10 hours
  4. extractionextracted twice with 50 ml of ethyl acetate
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customto give a crude product

Sources & evidence

ORD record
ord-70687ac8f35f4bbba818f91b2ef6515c
Source dataset
uspto-grants-1997_12
Patent number
US05698702

Reaction notes

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