Carbazole → 9-(8-Bromodibenzo[b,d]furan-2-yl)-9H-carbazole

HRID 1486375

Reaction equation

HRID 1486375 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Br[C:15]1[CH:28]=[CH:27][C:18]2[O:19][C:20]3[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][C:21]=3[C:17]=2[CH:16]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>[Cu].ClC1C=CC=CC=1Cl>[Br:26][C:23]1[CH:24]=[CH:25][C:20]2[O:19][C:18]3[CH:27]=[CH:28][C:15]([N:12]4[C:11]5[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=5[C:5]5[C:13]4=[CH:1][CH:2]=[CH:3][CH:4]=5)=[CH:16][C:17]=3[C:21]=2[CH:22]=1

Participants

7

Reactant 4

HCID 6854CarbazoleHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 822902,8-Dibromodibenzofuran

Product 1

HCID 575440429-(8-Bromodibenzo[b,d]furan-2-yl)-9H-carbazoleYield 30.4%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of carbazole (1.15 g, 6.87 mmol), 2,8-dibromodibenzo[b,d]furan (4.48 g, 13.74 mmol), copper powder (0.30 g, 4.58 mmol), potassium carbonate (3.80 g, 27.50 mmol), 18-crown-6 (0.61 g, 2.29 mmol), and 1,2-dichlorobenzene (50 mL) was degassed with bubbling argon for 45 min at 50° C. The reaction mixture was then heated to 200° C. and was stirred overnight (45 hours), maintaining an argon atmosphere. Production of decoupled material was shown by LCMS and the reaction was cooled to room temperature. The mixture was filtered, and the filtrate was dried. The copper was removed by a short silica gel plug with dichloromethane as the eluent, and the product was purified by silica gel column chromatography with toluene in hexanes as the eluent. The product fractions were then dried and the product was collected to yield Compound 12 (0.861 g, 30%). Confirmed by LCMS (APCI): calculated for C24H14BrNO (M+H): 412. Found: 412.

Workup

  1. customwas degassed with bubbling argon for 45 min at 50° C
  2. temperaturemaintaining an argon atmosphere
  3. temperaturethe reaction was cooled to room temperature
  4. filtrationThe mixture was filtered
  5. customthe filtrate was dried
  6. customThe copper was removed by a short silica gel plug with dichloromethane as the eluent
  7. customthe product was purified by silica gel column chromatography with toluene in hexanes as the eluent
  8. customThe product fractions were then dried
  9. customthe product was collected

Sources & evidence

ORD record
ord-37d839c0189b4a76802d7c6f988c0952
Source dataset
uspto-grants-2016_08
Patent number
US09425408B2

Linked notes

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