Carbazole → HCID 86723548, compound

HRID 2206818Notes

Reaction equation

HRID 2206818 reaction equation
Br[C:2]1[C:6]2[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1.[CH:12]1[C:24]2[NH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]=2[CH:15]=[CH:14][CH:13]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>[Cu]I.O1CCOCC1>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]2[S:4][CH:3]=[C:2]([N:23]3[C:24]4[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=4[C:17]4[C:22]3=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:6]=2[CH:7]=1

Participants

6

Reactant 3

HCID 6854CarbazoleHCID 62657Potassium Phosphate, TribasicHCID 142423383-Bromo-5-chlorobenzo[b]thiophene

Product 1

HCID 86723548HCID 86723548, compoundYield 129.4%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

In a 250 mL 2-neck round flask 3-bromo-5-chlorobenzothiophene (2 g, 8.1 mmol), carbazole (0.675 g, 4.05 mmol), CuI (0.46 g, 24.3 mmol), trans-1,2-dicyclohexane-diamine (0.92 g, 2.43 mmol), K3PO4 (3.43 g, 16.2 mmol), and 150 mL of 1,4-dioxane were poured, and refluxed and stirred. After the reaction, the solid matter was filtered. And after the organic solvent was distilled in vacuum and removed, column chromatography (Hex:E.A=9:1) is performed, the solution was distilled in vacuum, giving 1.75 g of white solid (65% yield).

Workup

  1. temperaturerefluxed
  2. customAfter the reaction
  3. filtrationthe solid matter was filtered
  4. distillationAnd after the organic solvent was distilled in vacuum
  5. customremoved
  6. distillationthe solution was distilled in vacuum

Sources & evidence

ORD record
ord-2603fd701a1b46179a1cc521a47b63df
Source dataset
uspto-grants-2016_06
Patent number
US09373794B2

Reaction notes

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