Sodium Carbonate → 3,6-Diphenylcarbazole

HRID 921600Notes

Reaction equation

HRID 921600 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.[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:25](=O)([O-])[O-].[Na+].[Na+].C(P([C:40]([CH3:43])([CH3:42])C)C(C)(C)C)(C)(C)C.O1[CH2:49][CH2:48]OCC1>O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:16]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:42]2[CH:40]=[CH:43][CH:49]=[CH:48][CH:25]=2)=[CH:9][CH:8]=4)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 66827Phenylboronic AcidHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 2748743,6-Dibromocarbazole

Product 1

HCID 31232953,6-DiphenylcarbazoleYield 80%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent

Procedure

25 g 3,6-dibromocarbazole and 20.5 g phenylboronic acid were mixed in 150 mL water and 300 mL dioxane in glove box. Stir vigorously and add 45 g sodium carbonate. Finally add 3 g Pd2DBA3 and 1.5 g tri-t-butylphosphine. Stir and reflux overnight then cool and remove from glove box. Add water to precipitate white solid then filter and collect. Dissolve in dichloromethane and chromatograph on silica eluting with DCM:hexanes 1:2 and elute product as colorless solution which on evaporation and washing with hexanes gives the desired product in ˜80% yield as a fluffy white solid.

Workup

  1. stirringStir
  2. temperaturereflux overnight
  3. temperaturethen cool
  4. customremove from glove box
  5. customAdd water to precipitate white solid
  6. filtrationthen filter
  7. customcollect
  8. dissolutionDissolve in dichloromethane
  9. washchromatograph on silica eluting with DCM:hexanes 1:2 and elute product as colorless solution which
  10. customon evaporation
  11. washwashing with hexanes

Sources & evidence

ORD record
ord-503c35f299f343deb7d3c9c241c8930e
Source dataset
uspto-grants-2016_03
Patent number
US09276217B2

Reaction notes

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