Potassium Carbonate → 3-(Dibenzofuran-2-yl)-9H-carbazole

HRID 1747205Notes

Reaction equation

HRID 1747205 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][CH:10]=[CH:9][CH:8]=3.[CH:15]1[C:23]2[C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[O:20][C:19]=2[CH:18]=[CH:17][C:16]=1B(O)O.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1.C(O)C>[CH:15]1[C:23]2[C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[O:20][C:19]=2[CH:18]=[CH:17][C:16]=1[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][CH:10]=[CH:9][CH:8]=3

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 2524463-BromocarbazoleHCID 12032376Dibenzo(b,d)furan-2-ylboronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 579976693-(Dibenzofuran-2-yl)-9H-carbazoleYield 27.8%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

Into a 300-mL three-neck flask were put 2.3 g (9.4 mmol) of 3-bromo-9H-carbazole, 2.0 g (9.4 mmol) of dibenzofuran-2-boronic acid, and 0.42 g (1.4 mmol) of tris(2-methylphenyl)phosphine. To the mixture were added 30 mL of ethanol, 50 mL of toluene, and 10 mL (2.0 mol/L) of an aqueous solution of potassium carbonate. This mixture was stirred to be degassed while the pressure was reduced. To this mixture was added 63 mg (0.28 mmol) of palladium(II) acetate. This mixture was stirred at 90° C. for 5 hours, cooled to room temperature, and then left for 15 hours; accordingly, a brown solid was precipitated. The precipitated solid was subjected to suction filtration and then collected. The collected solid was dissolved in about 30 mL of hot toluene, and this solution was suction-filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135). The resulting filtrate was concentrated to give a white solid. This solid was recrystallized with toluene/hexane to give 0.87 g of white powder in 27% yield. The synthesis scheme of Step 3 is shown in (a-3).

Workup

  1. customInto a 300-mL three-neck flask were put
  2. customto be degassed while the pressure
  3. stirringThis mixture was stirred at 90° C. for 5 hours
  4. customaccordingly, a brown solid was precipitated
  5. filtrationThe precipitated solid was subjected to suction filtration
  6. customcollected
  7. dissolutionThe collected solid was dissolved in about 30 mL of hot toluene
  8. filtrationthis solution was suction-filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135)
  9. concentrationThe resulting filtrate was concentrated
  10. customto give a white solid
  11. customThis solid was recrystallized with toluene/hexane

Sources & evidence

ORD record
ord-ab25c90b9cb440cea5e5998c39b6b958
Source dataset
uspto-grants-2015_10
Patent number
US09150551B2

Reaction notes

Loading…