1-Phenyl-1-propanone → Alpha-(4-methoxyphenyl)propiophenone

HRID 984743Notes

Reaction equation

HRID 984743 reaction equation
CC(C)([O-])C.[Na+].Br[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=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][O:14][C:11]1[CH:12]=[CH:13][C:8]([CH:17]([CH3:18])[C:16]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:19])=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 71481-Phenyl-1-propanoneHCID 77304-BromoanisoleHCID 23676156Sodium t-butoxide

Product 1

HCID 11096728Alpha-(4-methoxyphenyl)propiophenoneYield 79%

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), 4-bromoanisole (187 mg, 0.125 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 14 h. 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 (12:1 hexane:ethyl acetate was the eluent) gave 0.189 g (79%) of α-(4-methoxyphenyl)propiophenone, a white solid. 1H NMR (CDCl3, 300 MHz) a 7.96 (m, 2H); 7.48 (m, 1H); 7.39 (m, 2H); 7.21 (d, 2H, J=8.7 Hz); 6.84 (d; 2H, 8.7 Hz); 4.66 (q, 1H, J=6.9 Hz); 3.76 (s, 3H); 1.52 (d, 3H, J=6.9).

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

Sources & evidence

ORD record
ord-615109c2ad8943e58111e361431f241f
Source dataset
uspto-grants-2005_03
Patent number
US06867310B1

Reaction notes

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