Toluene → HCID 66724872, compound

HRID 1993090Notes

Reaction equation

HRID 1993090 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6](C3C=CC(C4C=CC=CC=4)=CC=3)[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.CC(C)([O-])C.[Na+].[C:33]1([CH3:40])[C:34](C)=[CH:35][CH:36]=[CH:37][CH:38]=1.[NH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.[C:48]1(C)[CH:53]=[CH:52]C=[CH:50][CH:49]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[Fe+2]>[C:40]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:52]=[CH:53][C:48]([C:13]2[C:5]3[NH:6][C:7]4[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:4]=3[CH:3]=[C:2]([NH:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH:14]=2)=[CH:49][CH:50]=1

Participants

8

Reactant 5

HCID 1140TolueneHCID 6115AnilineHCID 7237O-XyleneHCID 23676156Sodium t-butoxideHCID 534011059-([1,1'-Biphenyl]-4-yl)-3-bromo-9H-carbazole

Product 1

HCID 66724872HCID 66724872, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 152416121,1`-Bis(diphenylphosphino)ferroceneCatalyst

Conditions

Temperature
130 °C

Procedure

3.7 g (9.2 mmol) of 3-bromo-9-(4-biphenylyl)carbazole, 63 mg (0.3 mmol) of palladium acetate, 330 mg (0.6 mmol) of 1,1-bis(diphenylphosphino)ferrocene, and 1.5 g (15 mmol) of sodium-tert-butoxide were put in a three-neck flask and the atmosphere of the flask was substituted by nitrogen, and then, 20 mL of dehydrated xylene was added, and deaeration was performed. Then, 9.3 g (10 mmol) of aniline was added thereto. Under a nitrogen atmosphere, it was heated and stirred at 130° C. for 4 hours. After the termination of the reaction, about 300 mL of hot toluene was added to this suspension, and the mixture was filtered through florisil, alumina, and Celite®. The obtained filtrate was concentrated and hexane was added thereto. Then, it was precipitated by ultrasonic wave. This was filtered, and the residue was dried to obtain 3.5 g (yield: 93%) of N-[(4-biphenylyl)carbazol-3-yl]-N-phenylamine (BCA) which was cream-colored powder.

Workup

  1. temperatureUnder a nitrogen atmosphere, it was heated
  2. additionwas added to this suspension
  3. filtrationthe mixture was filtered through florisil, alumina, and Celite®
  4. concentrationThe obtained filtrate was concentrated
  5. additionhexane was added
  6. customThen, it was precipitated by ultrasonic wave
  7. filtrationThis was filtered
  8. customthe residue was dried

Sources & evidence

ORD record
ord-e63c52ea8016436d8fcf154a20cf722f
Source dataset
uspto-grants-2010_01
Patent number
US07649197B2

Reaction notes

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