Potassium Fluoride → Ethyl 2-[3-(3-thienyl)phenoxy]acetate

HRID 1464757Notes

Reaction equation

HRID 1464757 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[O:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].C([Sn](CCCC)(CCCC)[C:20]1[CH:24]=[CH:23][S:22][CH:21]=1)CCC.[F-].[K+]>C1(C)C(C)=CC=CC=1>[S:22]1[CH:23]=[CH:24][C:20]([C:2]2[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=2)[O:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:21]1

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 5197439Ethyl 2-(3-bromophenoxy)acetateHCID 10959689Stannane, tributyl-3-thienyl-

Product 1

HCID 19916940Ethyl 2-[3-(3-thienyl)phenoxy]acetateYield 64.6%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2.6 g of the resulting ether compound, 5.3 g of tri-n-butyl(3-thienyl)tin and 20 mg of tetrakis(triphenhylphosphine)paladium were dissolved in 10 ml of xylene, and the mixture was refluxed for 5.5 hours. A 25% aqueous solution of potassium fluoride was added to the solution, and then the precipitate was removed by filtration. The organic layer separated was worked up in a customary manner, and the product was purified by silica gel column chromatography [hexane/ethyl acetate=20/1→15/1] to give 1.7 g of ethyl 3-(3-thienyl)phenoxyacetate as a white powder.

Workup

  1. temperaturethe mixture was refluxed for 5.5 hours
  2. customthe precipitate was removed by filtration
  3. customThe organic layer separated
  4. customthe product was purified by silica gel column chromatography [hexane/ethyl acetate=20/1→15/1]

Sources & evidence

ORD record
ord-2f95f5fbb2154b268982ed175a7726e9
Source dataset
uspto-grants-1994_04
Patent number
US05306728

Reaction notes

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