Toluene → [3'-(3,6-Diphenylcarbazol-9-yl)biphenyl-3-yloxy]methane

HRID 1502190

Reaction equation

HRID 1502190 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]2[C:20]3[CH:19]=[CH:18][C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:16][C:15]=3[C:14]3[C:9]2=[CH:10][CH:11]=[C:12]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:13]=3)[CH:5]=[CH:6][CH:7]=1.[CH3:33][O:34][C:35]1[CH:36]=[C:37](B(O)O)[CH:38]=[CH:39][CH:40]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>O.C(Cl)Cl.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.C(O)C>[C:27]1([C:12]2[CH:11]=[CH:10][C:9]3[N:8]([C:4]4[CH:5]=[C:6]([C:37]5[CH:38]=[CH:39][CH:40]=[C:35]([O:34][CH3:33])[CH:36]=5)[CH:7]=[CH:2][CH:3]=4)[C:20]4[C:15]([C:14]=3[CH:13]=2)=[CH:16][C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:18][CH:19]=4)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

9

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 581422319-(3-bromophenyl)-3,6-diphenyl-9H-Carbazole

Product 1

HCID 66717069[3'-(3,6-Diphenylcarbazol-9-yl)biphenyl-3-yloxy]methaneYield 85.4%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The obtained 9-(3-bromophenyl)-3,6-diphenylcarbazole (3.20 g, 6.75 mmol), 3-methoxyphenylboronic acid (1.54 g, 10.1 mmol) and tetrakis(triphenylphosphine)palladium (0.124 g) were added to a solvent mixture of toluene (30 mL) and ethanol (10 mL). Then, an aqueous solution of sodium carbonate (37.3 g) in distilled water (90 mL) was added the mixture. The resultant mixture was refluxed for 9 hours in a nitrogen atmosphere and then cooled to room temperature. The obtained mixture was diluted with methylene chloride and the insoluble matter was removed through filtration. The organic layer was washed with water and separated. The solvent was evaporated under reduced pressure. The residue was purified through silica gel column chromatography using as an eluent a solvent mixture of methylene chloride/hexane (2/3 by volume), to thereby obtain 2.89 g of [3′-(3,6-diphenylcarbazol-9-yl)biphenyl-3-yloxy]methane.

Workup

  1. customthe insoluble matter was removed through filtration
  2. washThe organic layer was washed with water
  3. customseparated
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified through silica gel column chromatography
  6. additiona solvent mixture of methylene chloride/hexane (2/3 by volume)

Sources & evidence

ORD record
ord-31d2d8947f3d4766817a5f37423f0bd2
Source dataset
uspto-grants-2015_12
Patent number
US09206202B2

Linked notes

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