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

HRID 13903

Reaktionsgleichung

Reaktionsgleichung von HRID 13903
CC(C)([O-])C.[Na+].O1CCCC1.Br[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:19]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:22])[CH2:20][CH3:21]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC([B-](C2C=CC(C)=CC=2)(C2C=CC(C)=CC=2)C2C=CC(C)=CC=2)=CC=1.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.O>[C:23]1([C:19](=[O:22])[CH:20]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:21])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

8

Edukt 4

HCID 71481-Phenyl-1-propanoneHCID 7961BromobenzeneHCID 8028TetrahydrofuranHCID 23676156Sodium t-butoxide

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 23136639Tri-tert-butylphosphonium tetra-para-tolylborateKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A 30-ml four-necked flask was equipped with a stirrer, a thermometer and a reflux condenser. 0.011 g (0.05 mmol) of palladium (II) acetate, 1.442 g (15 mmol) of sodium-tert-butoxide and 10 ml of tetrahydrofuran were weighed in the flask, followed by stirring. Further, 0.029 g (0.05 mmol) of tri-tert-butylphosphonium tetra-para-tolylborate obtained in Example B-3 was weighed in air and added into the flask. The flask was purged with argon, followed by stirring at 25° C. for 30 minutes. 1.570 g (10 mmol) of bromobenzene was added, followed by stirring at 25° C. for 30 minutes. 1.476 g (11 mmol) of propiophenone was added, followed by stirring at 25° C. for 17 hours. After the completion of the reaction, 5 ml of water was added, followed by separation. The organic phase was purified by column chromatography to afford 2.061 g of 1,2-diphenyl-1-propanone (yield: 98 mol % based on bromobenzene). The identification of the product was made by mass spectroscopy, 1H-NMR and 13C-NMR.

Aufarbeitung

  1. customA 30-ml four-necked flask was equipped with a stirrer
  2. additionadded into the flask
  3. customThe flask was purged with argon
  4. stirringby stirring at 25° C. for 30 minutes
  5. stirringby stirring at 25° C. for 30 minutes
  6. stirringby stirring at 25° C. for 17 hours
  7. additionwas added
  8. customfollowed by separation
  9. customThe organic phase was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-95e39380ae354ac0977ad604490c471f
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728176B2

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