Ethanol → 3,6-Bis(4-(octyloxy)phenyl)-carbazole

HRID 1897376Notes

Reaction equation

HRID 1897376 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.[CH2:16]([O:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[C:34]([O-:37])(O)=O.[Na+].[CH2:39](O)[CH3:40]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH2:16]([O:24][C:25]1[CH:30]=[CH:29][C:28]([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:2]2[CH:3]=[CH:4][C:5]([O:37][CH2:34][CH2:9][CH2:8][CH2:7][CH2:12][CH2:11][CH2:39][CH3:40])=[CH:13][CH:14]=2)=[CH:9][CH:8]=4)=[CH:27][CH:26]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

7

Reactant 4

HCID 702EthanolHCID 2748743,6-DibromocarbazoleHCID 516892Sodium BicarbonateHCID 39772844-n-Octyloxyphenylboronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 684414343,6-Bis(4-(octyloxy)phenyl)-carbazole

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

3,6-dibromocarbazole (3.03 g, 9.32 mmol), 4-(octyloxy)phenylboronic acid (7.14 g, 28.5 mmol), aqueous NaHCO3 (80 ml), ethanol (120 ml) and toluene (190 ml) was mixed and degassed with nitrogen for 15 minutes before adding the Pd(PPh3)4 catalyst (80 mg, 0.07 mmol). The reaction mixture was then brought to reflux at 90° C. for 5 h 20 minutes. It was quenched with water when reached room temperature and extracted three times with ethyl acetate. The combined organic phases were washed with brine and water and evaporated. The residual solid was dissolved in toluene and precipitated in petroleum ether. The precipitate was purified using column chromatography with toluene as mobile phase which yielded 3,6-bis(4-(octyloxy)phenyl)-carbazole (5.42 g, 9.41 mmol) as a white solid.

Workup

  1. customdegassed with nitrogen for 15 minutes
  2. customIt was quenched with water when
  3. customreached room temperature
  4. extractionextracted three times with ethyl acetate
  5. washThe combined organic phases were washed with brine and water
  6. customevaporated
  7. dissolutionThe residual solid was dissolved in toluene
  8. customprecipitated in petroleum ether
  9. customThe precipitate was purified

Sources & evidence

ORD record
ord-0629ef9883f74e619f4cadf5a6f680be
Source dataset
uspto-grants-2013_08
Patent number
US08519037B2

Reaction notes

Loading…