2-Phenylacetophenone → Benzofurans

HRID 1893106Notes

Reaction equation

HRID 1893106 reaction equation
[C:1]1([C:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC1C=CC=CC=1C>[C:1]1([C:7]2[O:8][C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:9]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 99482-PhenylacetophenoneHCID 10796Cesium carbonateHCID 114141,2-DibromobenzeneHCID 11776Triphenylphosphine

Product 1

HCID 253613BenzofuransYield 80.7%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7237O-XyleneSolvent

Procedure

39.2 g of benzyl phenyl ketone, 46.7 g of 1,2-dibromobenzene, g of palladium acetate, 10.5 g of triphenylphosphine, 77.2 g of cesium carbonate, and 400 mL of o-xylene were loaded into a flask, and the mixture was refluxed and stirred under heat under an argon atmosphere for 8 hours. After the completion of the reaction, the reaction solution was filtrated while being extracted with ether. The filtrate was dried with magnesium sulfate, and was then concentrated. The residue was purified by silica gel column chromatography, whereby 43.2 g of a white crystal were obtained (80% yield).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heat under an argon atmosphere for 8 hours
  3. customAfter the completion of the reaction
  4. filtrationthe reaction solution was filtrated
  5. extractionwhile being extracted with ether
  6. dry with materialThe filtrate was dried with magnesium sulfate
  7. concentrationwas then concentrated
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0b22d1ef6f82485cb7e16e9087c5a57c
Source dataset
uspto-grants-2013_08
Patent number
US08512875B2

Reaction notes

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