Potassium Carbonate → HCID 21466543, compound

HRID 1940244Notes

Reaction equation

HRID 1940244 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](O)[CH:5]=[C:6]([Cl:20])[C:7]=1[O:8][C:9]1[C:14]([Br:15])=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][N:10]=1.[C:22](=[O:25])([O-])[O-].[K+].[K+].[Cl:28][C:29]([Cl:33])=[CH:30]CCl>CN(C)C=O>[Cl:1][C:2]1[C:3]([O:25][CH2:22][CH:30]=[C:29]([Cl:33])[Cl:28])=[CH:4][CH:5]=[C:6]([Cl:20])[C:7]=1[O:8][C:9]1[C:14]([Br:15])=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 173781,1,3-TrichloropropeneHCID 21466420HCID 21466420, compound

Product 1

HCID 21466543HCID 21466543, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 0.83 g of 3,5-dichloro-4-(3-bromo-5-trifluoromethyl-2-pyridyloxy)phenol, 0.31 g of potassium carbonate and 20 ml of N-dimethylformamide, a solution prepared by dissolving 0.33 g of 1,1,3-trichloro-1-propene in 5 ml of N,N-dimethylformamide was added dropwise at room temperature with stirring. After stirring at room temperature for 7 hours, the reaction solution was poured into ice-water, and extracted twice with 50 mi of diethyl ether. Then, the ether 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 0.79 g of 3,5-dichloro-4-(3-bromo-5-trifluoromethyl-2-pyridyloxy)-2-(3,3-dichloro-2-propenyloxy)benzene, yield 75%; m.p., 90.7° C.

Workup

  1. customa solution prepared
  2. additionwas added dropwise at room temperature
  3. stirringAfter stirring at room temperature for 7 hours
  4. extractionextracted twice with 50 mi of diethyl ether
  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-7a70ab499a624950a10ceb16c01b54c3
Source dataset
uspto-grants-1997_12
Patent number
US05698702

Reaction notes

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