Sodium Carbonate → 4-Bromo-4'-(diphenylamino)biphenyl

HRID 1618830

Reaktionsgleichung

Reaktionsgleichung von HRID 1618830
[C:1]1([N:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:24]1[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][CH:25]=1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:30][C:27]1[CH:28]=[CH:29][C:24]([C:11]2[CH:12]=[CH:13][C:8]([N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:9][CH:10]=2)=[CH:25][CH:26]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 115221-Bromo-4-iodobenzeneHCID 121669344-(Diphenylamino)phenylboronic Acid (contains varying amounts of Anhydride)

Produkt 1

HCID 113155504-Bromo-4'-(diphenylamino)biphenylAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

A mixture of (4-(diphenylamino)phenyl)boronic acid (1.5 g, 5.19 mmol), 4-iodo-1-bromobenzene (1.33 g, 4.71 mmol), Na2CO3 (1.78 g, 16.8 mmol) and Pd(PPh3)4 (0.163 g, 0.141 mmol) in THF/H2O (28 mL/17 mL) was degassed and the resulting mixture was heated at reflux overnight under an argon atmosphere. After cooling, the mixture was poured into dichloromethane (150 mL), then washed with water (2×150 mL) and brine (100 mL). The organic phase was dried over Na2SO4, purified with flash column chromatography (silica gel, hexanes/ethyl acetate 50:1) then recrystallized in dichloromethane/methanol to afford a white solid (Compound 35)(1.64 g, in 87% yield).

Aufarbeitung

  1. customwas degassed
  2. temperaturethe resulting mixture was heated
  3. temperatureat reflux overnight under an argon atmosphere
  4. temperatureAfter cooling
  5. additionthe mixture was poured into dichloromethane (150 mL)
  6. washwashed with water (2×150 mL) and brine (100 mL)
  7. dry with materialThe organic phase was dried over Na2SO4
  8. custompurified with flash column chromatography (silica gel, hexanes/ethyl acetate 50:1)
  9. customthen recrystallized in dichloromethane/methanol

Quellen und Nachweise

ORD-Eintrag
ord-d9dab75fdf0149dc920fa6231f79db7c
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08771845B2

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