Chlorobenzene → Triphenylamine

HRID 13886

Reaktionsgleichung

Reaktionsgleichung von HRID 13886
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]1([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CC(C)([O-])C.[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1([B-](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.C1(C)C(C)=CC=CC=1>[C:2]1([N:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 3

HCID 7964ChlorobenzeneHCID 11487DiphenylamineHCID 23676156Sodium t-butoxide

Produkt 1

HCID 11775TriphenylamineAusbeute 91,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 23136663Tri-tert-butylphosphonium TetraphenylborateKatalysatorHCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

A 100-ml four-necked flask was equipped with a stirrer, a thermometer and a reflux condenser. 5.403 g (48 mmol) of chlorobenzene, 6.769 g (40 mmol) of diphenylamine, 4.613 g (48 mmol) of sodium-tert-butoxide, 0.002 g (0.01 mmol) of palladium (II) acetate and 5 ml of xylene were weighed in the flask, followed by stirring. Further, 0.021 g (0.04 mmol) of tri-tert-butylphosphonium tetraphenylborate obtained in Example A-1 was weighed in air and added into the flask. The flask was purged with argon, followed by stirring at 100-120° C. for 10 hours. After the completion of the reaction, 45 ml of xylene and 50 ml of saturated sodium chloride solution were added, followed by separation. The organic phase was purified by column chromatography to afford 9.008 g of triphenylamine (yield: 92 mol % based on diphenylamine). The melting point was 125-126° C.

Aufarbeitung

  1. customA 100-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 100-120° C. for 10 hours
  5. customAfter the completion of the reaction, 45 ml of xylene and 50 ml of saturated sodium chloride solution
  6. additionwere added
  7. customfollowed by separation
  8. customThe organic phase was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6c6131f7f7fc4152b71a387511cff45e
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728176B2

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