Toluene → HCID 71238684, compound

HRID 1502193Notes

Reaction equation

HRID 1502193 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3.[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1(C)C=CC=CC=1>C(O)C>[Br:15][C:10]1[CH:9]=[CH:8][C:7]2[N:6]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)[C:5]3[C:13]([C:12]=2[CH:11]=1)=[CH:14][C:2]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH:3][CH:4]=3

Participants

5

Reactant 3

HCID 1140TolueneHCID 66827Phenylboronic AcidHCID 534010773,6-Dibromo-9-(4-methylphenyl)-9H-carbazole

Product 1

HCID 71238684HCID 71238684, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,6-Dibromo-N-(4-methylphenyl)carbazole (6.23 g) and phenylboronic acid (2.01 g) were added to a solvent mixture of toluene (60 mL) and ethanol (15 mL), followed by bubbling with nitrogen. Then, tetrakistriphenylphosphine palladium (290 mg) and 21.2% aqueous sodium carbonate solution (15.0 g) were added to the mixture, and the resultant mixture was refluxed under nitrogen flow for 5 hours. The mixture was diluted with toluene. The toluene layer was washed with water and dried and the toluene was evaporated. The residue was treated through silica gel column chromatography (eluent: toluene/hexane=1/4 (by mass)), to thereby obtain 3.20 g of 3-bromo-6-phenyl-N-(4-methylphenyl)carbazole as colorless powder.

Workup

  1. customby bubbling with nitrogen
  2. additionThen, tetrakistriphenylphosphine palladium (290 mg) and 21.2% aqueous sodium carbonate solution (15.0 g) were added to the mixture
  3. temperaturethe resultant mixture was refluxed under nitrogen flow for 5 hours
  4. additionThe mixture was diluted with toluene
  5. washThe toluene layer was washed with water
  6. customdried
  7. customthe toluene was evaporated
  8. additionThe residue was treated through silica gel column chromatography (eluent: toluene/hexane=1/4 (by mass))

Sources & evidence

ORD record
ord-575baa2aace94c44ad6a14d54e804c2f
Source dataset
uspto-grants-2015_12
Patent number
US09206202B2

Reaction notes

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