Nitrobenzene → HCID 131734301, compound

HRID 1502191Notes

Reaction equation

HRID 1502191 reaction equation
C1([Si](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC([C:14]3[CH:15]=[CH:16][C:17]4[NH:18][C:19]5[C:24]([C:25]=4[CH:26]=3)=[CH:23][C:22](C3C=CC([Si](C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)=CC=3)=[CH:21][CH:20]=5)=CC=2)C=CC=CC=1.[OH:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][O:73][C:74]1[CH:79]=[CH:78][C:77](I)=[CH:76][CH:75]=1.C(=O)([O-])[O-].[K+].[K+].[N+](C1C=CC=CC=1)([O-])=O>[Cu]>[OH:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][O:73][C:74]1[CH:79]=[CH:78][CH:77]=[CH:76][C:75]=1[C:26]1[C:25]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][C:17]=2[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 7416NitrobenzeneHCID 11430Potassium CarbonateHCID 71238547HCID 71238547, compoundHCID 89396454HCID 89396454, compound

Product 1

HCID 131734301HCID 131734301, compound

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

The 3,6-bis(4-triphenylsilylphenyl)carbazole (1.30 g), 4-(8-hydroxyoctyloxy)iodobenzene (0.65 g), potassium carbonate (0.54 g), copper powder (0.4 g) and nitrobenzene (5 mL) were stirred under nitrogen flow at 195° C. for 16 hours. The resultant mixture was filtrated through CELITE and the solvent was evaporated. The residue was treated through silica gel column chromatography (eluent: 10% ethyl acetate/toluene solution), to thereby obtain 1.50 g (89.8%) of 3,6-bis(4-triphenylsilylphenyl)-N-[4-(8-hydroxyoctyloxyphenyl]carbazole as colorless needle crystals.

Workup

  1. filtrationThe resultant mixture was filtrated through CELITE
  2. customthe solvent was evaporated
  3. additionThe residue was treated through silica gel column chromatography (eluent: 10% ethyl acetate/toluene solution)

Sources & evidence

ORD record
ord-fca5e7a5bbbc44c7b077a4c8c7d1252c
Source dataset
uspto-grants-2015_12
Patent number
US09206202B2

Reaction notes

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