Nitrogen → N-(4-tert-Butylphenyl)-2,7-dibromocarbazole

HRID 555929

Reaction equation

HRID 555929 reaction equation
N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.N#N.[Br:17][C:18]1[CH:30]=[CH:29][C:28]2[C:27]3[C:22](=[CH:23][C:24]([Br:31])=[CH:25][CH:26]=3)[NH:21][C:20]=2[CH:19]=1.I[C:33]1[CH:38]=[CH:37][C:36]([C:39]([CH3:42])([CH3:41])[CH3:40])=[CH:35][CH:34]=1>C1(C)C=CC=CC=1.[Cu]Cl.O>[C:39]([C:36]1[CH:37]=[CH:38][C:33]([N:21]2[C:22]3[CH:23]=[C:24]([Br:31])[CH:25]=[CH:26][C:27]=3[C:28]3[C:20]2=[CH:19][C:18]([Br:17])=[CH:30][CH:29]=3)=[CH:34][CH:35]=1)([CH3:42])([CH3:41])[CH3:40]

Participants

8

Reactant 4

HCID 947NitrogenHCID 13181,10-PhenanthrolineHCID 1420291-tert-Butyl-4-iodobenzeneHCID 111515032,7-Dibromocarbazole

Product 1

HCID 59557277N-(4-tert-Butylphenyl)-2,7-dibromocarbazole

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

A degassed solution of 489.5 mg (0.156%) of copper(I) chloride and 906 mg (1%) mmol) of 1,10-phenanthroline in 100 ml of toluene were saturated with N2 for 1 hour and heated to 130° C. The solution was subsequently admixed with 16.2 g (50 mmol) of 2,7-dibromocarbazole and 13.2 g (50 mmol) of 1-iodo-4-tert-butylbenzene and heated at 180° C. for 2 hours. After cooling, the mixture was admixed with 180 ml of water, the organic phase was separated off and the solvent was removed under reduced pressure. The product was recrystallized from n-hexane. Yield: 13 g (59%). Purity according to HPLC: 99.5%

Workup

  1. temperatureheated at 180° C. for 2 hours
  2. temperatureAfter cooling
  3. customthe organic phase was separated off
  4. customthe solvent was removed under reduced pressure
  5. customThe product was recrystallized from n-hexane

Sources & evidence

ORD record
ord-5d278e7e266b4969a7763f8bd154691b
Source dataset
uspto-grants-2011_11
Patent number
US08053547B2

Linked notes

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