1-Phenyl-1-propanone → 2-(2-Methylphenyl)-1-phenylpropan-1-one

HRID 984742Notes

Reaction equation

HRID 984742 reaction equation
CC(C)([O-])C.[Na+].Br[C:8]1[CH:9]=[C:10]([CH3:14])[CH:11]=[CH:12][CH:13]=1.[C:15]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:18])[CH2:16][CH3:17]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:14][C:10]1[CH:11]=[CH:12][CH:13]=[CH:8][C:9]=1[CH:16]([CH3:17])[C:15]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:18]

Participants

5

Reactant 3

HCID 71481-Phenyl-1-propanoneHCID 115603-BromotolueneHCID 23676156Sodium t-butoxide

Product 1

HCID 144492012-(2-Methylphenyl)-1-phenylpropan-1-oneYield 46%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

An oven dried Schlenk tube equipped with a rubber septum was cooled under an argon purge. The septum was removed and the tube was charged with palladium acetate (2.3 mg, 0.01 mmol) and sodium t-butoxide (125 mg, 1.3 mmol). The tube was capped with the septum, purged with argon. Toluene (2 mL) was added and the mixture stirred for 1 min at room temperature. 3-Bromotoluene (0.120 mL, 1.0 mmol) and propiophenone (0.16 mL, 1.2 mmol) were added to the tube. The mixture was heated to 80° C. and stirred until the starting halide had been completely consumed, as judged by GC analysis. The mixture was cooled to room temperature, quenched with saturated aqueous ammonium chloride (10 mL) and diluted with ether (20 mL). The mixture was poured into a separatory funnel and the layers were separated. The aqueous layer was extracted with ether (20 mL), the combined organic layers were washed with brine (20 mL), dried over anhydrous magnesium sulfate filtered and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel to afford 103 mg (46%) of α-(2-Methylphenyl)propiophenone. 1H NMR (CDCl3, 300 MHz) 7.81-7.84 (m, 2H), 7.47-6.99 (m, 71), 4.75 (q, 3=6.9 Hz, 1H), 2.49 (s, 3H), 1.46 (d, J=6.9 Hz, 3H) ppm.

Workup

  1. customAn oven dried Schlenk tube
  2. customequipped with a rubber septum
  3. temperaturewas cooled under an argon
  4. custompurge
  5. customThe septum was removed
  6. customThe tube was capped with the septum
  7. custompurged with argon
  8. additionToluene (2 mL) was added
  9. temperatureThe mixture was heated to 80° C.
  10. customhad been completely consumed
  11. temperatureThe mixture was cooled to room temperature
  12. customquenched with saturated aqueous ammonium chloride (10 mL)
  13. additiondiluted with ether (20 mL)
  14. additionThe mixture was poured into a separatory funnel
  15. customthe layers were separated
  16. extractionThe aqueous layer was extracted with ether (20 mL)
  17. washthe combined organic layers were washed with brine (20 mL)
  18. dry with materialdried over anhydrous magnesium sulfate
  19. filtrationfiltered
  20. concentrationconcentrated in vacuo
  21. customThe crude material was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-2f9a38affcfb49c7b22004af3165cff5
Source dataset
uspto-grants-2005_03
Patent number
US06867310B1

Reaction notes

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