Potassium Carbonate → HCID 53643449, compound

HRID 363061Notes

Reaction equation

HRID 363061 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:16])[CH:5]=[C:6]([Cl:15])[C:7]=1[O:8][C:9]([F:14])([F:13])[CH:10]([F:12])[F:11].C(=O)([O-])[O-].[K+].[K+].[Cl:23][C:24]([Cl:28])=[CH:25][CH2:26]Cl>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([O:16][CH2:26][CH:25]=[C:24]([Cl:28])[Cl:23])[CH:5]=[C:6]([Cl:15])[C:7]=1[O:8][C:9]([F:14])([F:13])[CH:10]([F:12])[F:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 173781,1,3-TrichloropropeneHCID 54015144HCID 54015144, compound

Product 1

HCID 53643449HCID 53643449, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 600 mg of 3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenol, 330 mg of potassium carbonate and 10 ml of N,N-dimethylformamide was added dropwise a solution of 340 mg of 1,1,3-trichloro-1-propene dissolved in 3 ml of N,N-dimethylformamide, while stirring at room temperature. After stirring continued at room temperature for 5 hours, the reaction mixture was poured into ice-water, and extracted twice with 40 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 630 mg of 3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene (82% yield), nD24.6 1.5067.

Workup

  1. stirringAfter stirring
  2. extractionextracted twice with 40 ml of diethyl ether
  3. washThe combined ether layer was washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customto obtain a crude product

Sources & evidence

ORD record
ord-b0c8cf2550c147f08410b9d2dcfe3e77
Source dataset
uspto-grants-1999_02
Patent number
US05872137

Reaction notes

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