Potassium Carbonate → HCID 54276837, compound

HRID 363065Notes

Reaction equation

HRID 363065 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].C(=O)([O-])[O-].[K+].[K+].[F:22][C:23]1[CH:30]=[CH:29][C:28]([O:31][C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)=[CH:27][C:24]=1[CH2:25]Br>CN(C)C=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][CH2:25][C:24]1[CH:27]=[C:28]([O:31][C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[CH:29]=[CH:30][C:23]=1[F:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 113467384-(3,3-Dichloro-2-propenyloxy)-2,6-dichlorophenolHCID 54061402HCID 54061402, compound

Product 1

HCID 54276837HCID 54276837, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 0.51 g of 2,6-dichloro-4-(3,3,-dichloro-2-propenyloxy)phenol, 0.17 g of potassium carbonate and 20 ml of N,N-dimethylformamide was added dropwise a solution of 0.34 g of 2-fluoro-5-(4-fluorophenoxy)benzyl bromide dissolved in 5 ml of N,N-dimethylformamide, while stirring at room temperature. After stirring at room temperature for 24 hours, the reaction mixture was poured into ice-water, and extracted twice with 50 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 0.50 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(2-fluoro-5-(4-fluorophenoxy) benzyloxy)benzene (68% yield), nD26.0 1.5871.

Workup

  1. stirringAfter stirring at room temperature for 24 hours
  2. extractionextracted twice with 50 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-1a2a4b0e365548bab345a719be1ec4da
Source dataset
uspto-grants-1999_02
Patent number
US05872137

Reaction notes

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