Water → HCID 15671396, compound

HRID 2079200Notes

Reaction equation

HRID 2079200 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][CH2:8][CH2:9]I.[F:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.O>CN(C=O)C.C(OCC)C>[F:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:9][CH2:8][F:7])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 69804Ethane, 1-fluoro-2-iodo-

Product 1

HCID 15671396HCID 15671396, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

After adding 7.34 g of potassium carbonate and 8.31 g of 1-fluoro-2-iodoethane to a solution of 4.5 g of 4-fluorophenol in 50 ml of DMF, the mixture was stirred at room temperature for 27 hours. Water was added to the reaction mixture, and extraction was performed with diethyl ether. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (4.6 g) as a colorless liquid.

Workup

  1. washThe organic layer was washed with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationThe desiccating agent was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-39dfcc0be2d64fd3b9fd848a52bd1134
Source dataset
uspto-grants-2011_04
Patent number
US07928228B2

Reaction notes

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