1-Phenyl-1-propanone → 1,2-Diphenylpropan-1-one

HRID 1421111Notes

Reaction equation

HRID 1421111 reaction equation
CC([O-])(C)C.[Na+].Br[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:14]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:17])[CH2:15][CH3:16]>C1COCC1.CCOCC.CC([O-])=O.CC([O-])=O.[Pd+2].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[C:18]1([C:14](=[O:17])[CH:15]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH3:16])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 3

HCID 71481-Phenyl-1-propanoneHCID 7961BromobenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 2385181,2-Diphenylpropan-1-oneYield 98%

Reagents, catalysts & solvents 4

HCID 83681Tris(1,1-dimethylethyl)phosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Reaction using 0.005 mol % catalyst: Pd(OAc)2 (0.5 mg, 0.0023 mmol), tri-t-butylphosphine (0.4 mg, 0.0020 mmol) and NaOtBu (5.80 g, 60.3 mmol) were suspended in 5 mL of THF in a screw-capped test tube. Bromobenzene (6.28 g, 40.0 mmol) and propiophenone (5.90 g, 44.0 mmol) were added to the reaction mixture in the drybox. The reaction tube was sealed with a cap and the mixture was stirred for 24 h at 60° C. The reaction was diluted with ether and washed with water and brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was chromatographed on silica gel (hexane/EtOAc=95/5) to give 8.2 g (98%) of 1,2-Diphenyl-1-propanone.

Workup

  1. customReaction
  2. customThe reaction tube was sealed with
  3. customa cap
  4. washwashed with water and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed on silica gel (hexane/EtOAc=95/5)

Sources & evidence

ORD record
ord-9ca4114fccb44541adc1d23874750273
Source dataset
uspto-grants-2000_06
Patent number
US06072073

Reaction notes

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