4-Bromodiphenyl Ether → 1-(4-Phenoxyphenyl)propan-2-one

HRID 849362

Reaction equation

HRID 849362 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([O:7][C:8]2[CH:13]=[CH:12][C:11](Br)=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.C[O-].C([Sn+](CCCC)CCCC)CCC.C([O:33][C:34]([CH3:36])=[CH2:35])(=O)C.[F-].[K+]>C1(C)C=CC=CC=1>[O:7]([C:8]1[CH:13]=[CH:12][C:11]([CH2:35][C:34](=[O:33])[CH3:36])=[CH:10][CH:9]=1)[C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

6

Reactant 4

HCID 75654-Bromodiphenyl EtherHCID 7916Isopropenyl acetateHCID 522689Potassium FluorideHCID 11964040Methoxytri-n-butylstannane

Product 1

HCID 195915231-(4-Phenoxyphenyl)propan-2-oneYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

75.0 g of 4-bromodiphenyl ether, 129 ml of tributyltin methoxide, 45.0 g of isopropenyl acetate and 2,47 g of dichlorobis{tri(o-tolyl)phosphine}palladium, were dissolved in 300 ml of toluene and refluxed under heating for 3 hours. The reaction solution was left to cool to room temperature, and then, a saturated potassium fluoride aqueous solution was added, followed by stirring for one hour. Then, the product was subjected to celite filtration and washed with ethyl acetate. The filtrate and washing liquid were put together. Then, the organic layer was separated and washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The drying agent was filtered off, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=15/1→10/1) to obtain 56.3 g (yield: 83%) of the above identified compound as yellow solid.

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 3 hours
  3. waitThe reaction solution was left
  4. filtrationThen, the product was subjected to celite filtration
  5. washwashed with ethyl acetate
  6. washThe filtrate and washing liquid
  7. customThen, the organic layer was separated
  8. washwashed with a saturated sodium chloride aqueous solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationThe drying agent was filtered off
  11. distillationthe solvent was distilled off under reduced pressure
  12. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=15/1→10/1)
  13. customto obtain 56.3 g (yield: 83%) of the

Sources & evidence

ORD record
ord-16f48f99f052458ab881bcbd42a77a81
Source dataset
uspto-grants-2000_01
Patent number
US06011174

Linked notes

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