1-Phenyl-1-propanone → HCID 22558559, compound

HRID 984744Notes

Reaction equation

HRID 984744 reaction equation
[CH3:1]C(C)([O-])C.[Na+].BrC1[CH:9]=[C:10]([CH3:15])[CH:11]=[C:12]([CH3:14])[CH:13]=1.[C:16]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:19])[CH2:17][CH3:18]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1>[CH3:15][C:10]1[CH:9]=[C:18]([CH:17]([CH3:1])[C:16]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:19])[CH:13]=[C:12]([CH3:14])[CH:11]=1

Participants

6

Reactant 3

HCID 71481-Phenyl-1-propanoneHCID 136357Benzene, 1-bromo-3,5-dimethyl-HCID 23676156Sodium t-butoxide

Product 1

HCID 22558559HCID 22558559, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A dry Schlenk tube was charged with Pd(OAc)2 (2.2 mg, 0.01 mmol) and sodium tert-butoxide (125 mg, 1.3 mmol). The tube was then evacuated and filled with argon. Toluene (1 mL), 5-bromo-m-xylene (185 mg, 0.136 mL, 1.0 mmol) and propiophenone (161 mg, 0.160 mL, 1.2 mmol) were sequentially added with a syringe, and the tube was sealed and heated in an oil bath at 80° C. for 2 h 20 min. The mixture was cooled, and partitioned between ether and water. The aqueous layer was extracted twice with ether, and the combined organics were dried over Na2SO4, filtered and concentrated. Chromatography on silica gel, eluting first with hexane, then 4:1 toluene: hexane, gave 0.198 g (83%) of α-(3,5-dimethylphenyl)propiophenone, a clear oil. 1H NMR (CDCl3, 300 MHz) δ 7.96 (m, 2H); 7.48 (m, 1H); 7.38 (m, 2H); 6.89 (s, 2H); 6.83 (s, 2H); 4.60 (q, 1H, J=6.9 Hz); 2.26 (s, 6H); 1.50 (d, 3H, J=6.9 Hz).

Workup

  1. customThe tube was then evacuated
  2. additionfilled with argon
  3. customthe tube was sealed
  4. temperatureThe mixture was cooled
  5. custompartitioned between ether and water
  6. extractionThe aqueous layer was extracted twice with ether
  7. dry with materialthe combined organics were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. washChromatography on silica gel, eluting first with hexane

Sources & evidence

ORD record
ord-067654e4ccf44e12aa4bd265a6b83215
Source dataset
uspto-grants-2005_03
Patent number
US06867310B1

Reaction notes

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