Acetophenone → 2-Phenylacetophenone

HRID 1421109Notes

Reaction equation

HRID 1421109 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:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])[CH3:15]>C1COCC1.CCOCC.CC([O-])=O.CC([O-])=O.[Pd+2].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[C:17]1([C:14](=[O:16])[CH2:15][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 3

HCID 7410AcetophenoneHCID 7961BromobenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 99482-PhenylacetophenoneYield 96%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
25 °C

Procedure

Pd(OAc)2 (2.3 mg, 0.010 mmol), tri-t-butylphosphine (2.1 mg, 0.010 mmol) and NaOtBu (211 mg, 2.20 mmol) were suspended in 1 mL of THF in a screw-capped vial. The vial was sealed with a cap containing a PTFE septum and removed from the dry box. Bromobenzene (157 mg, 1.00 mmol) and acetophenone (132 mg, 1.10 mmol) were added to the reaction mixture by syringe. The reaction mixture was stirred at 25° C. and monitored by GC analysis. The crude reaction was diluted with ether and washed with 1N HCl, 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 188 mg (96%) of 1,2-Diphenyl-1-ethanone: 1H NMR: (CDCl3) δ 8.02 (d, J=7.1 Hz, 2H), 7.58-7.26 (m, 8H), 4.31 (s, 2H); 13C{1H} NMR: (CDCl3) δ 197.52, 136.79, 134.67, 133.09, 129.54, 129.50, 128.64, 128.62, 126.88, 45.50.

Workup

  1. customThe vial was sealed with a cap
  2. customremoved from the dry box
  3. customThe crude reaction
  4. washwashed with 1N HCl, 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-a72426d05ed1486184ee16e798d2c44a
Source dataset
uspto-grants-2000_06
Patent number
US06072073

Reaction notes

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