1,2-Dimethoxyethane → 3,6-Diphenylcarbazole

HRID 433844Notes

Reaction equation

HRID 433844 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10](Br)=[CH:9][CH:8]=3.CO[CH2:18][CH2:19]OC.[C:22]1(OB(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:22]1([C:2]2[CH:3]=[CH:4][C:5]3[NH:6][C:7]4[C:12]([C:13]=3[CH:14]=2)=[CH:11][C:10]([C:19]2[CH:18]=[CH:13][CH:14]=[CH:2][CH:3]=2)=[CH:9][CH:8]=4)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 2748743,6-Dibromocarbazole

Product 1

HCID 31232953,6-Diphenylcarbazole

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In a 250 milliliter round bottom flask there were added 3,6-dibromocarbazole (5 grams), 50 milliliters of 1,2-dimethoxyethane, phenylboric acid (4.8 grams) dissolved in ethanol, and sodium carbonate (4.2 grams) dissolved in 20 milliliters of water. After the resulting solution was saturated with argon, 0.49 gram of tetrakis-(triphenylphosphine) palladium was added. The reaction mixture was heated to reflux and stirred for 18 hours. The reaction flask was removed from the heat and cooled to room temperature, about 22° C. to about 25° C. The resulting solution was transferred to a separatory funnel, and the organic layer, which contained product, was separated from the aqueous phase. After removal of the organic solvents by evaporation, the residue was subjected to column chromatography on silica gel to yield 3.5 grams of 3,6-diphenyl carbazole as colorless powder product. Its chemical structure was confirmed by Proton IR analysis.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux
  4. customThe reaction flask was removed from the
  5. temperatureheat
  6. customThe resulting solution was transferred to a separatory funnel
  7. customwas separated from the aqueous phase
  8. customAfter removal of the organic solvents
  9. customby evaporation

Sources & evidence

ORD record
ord-f8573b6937eb41e9a9a96386735443cf
Source dataset
uspto-grants-2003_12
Patent number
US06670054B1

Reaction notes

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