1,2-Diaminocyclohexane, trans- → 3-bromo-9-(dibenzo[b,d]furan-2-yl)-9H-carbazole

HRID 879916

Reaction equation

HRID 879916 reaction equation
[Br: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.I[C:16]1[CH:28]=[CH:27][C:19]2[O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:18]=2[CH:17]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C@@H]1(N)CCCC[C@H]1N>[Cu]I.O1CCOCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:24]3[CH:25]=[CH:26][C:21]4[O:20][C:19]5[CH:27]=[CH:28][CH:16]=[CH:17][C:18]=5[C:22]=4[CH:23]=3)[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 2233272-IododibenzofuranHCID 2524463-Bromocarbazole

Product 1

HCID 585110013-bromo-9-(dibenzo[b,d]furan-2-yl)-9H-carbazoleYield 56.3%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of 8.9 g (36.2 mmole) 3-bromo-9H-carbazole, 10.6 g (36.2 mmole) of 2-iododibenzo[b,d]furan, 17.1 g (90 mmole) of copper(I) iodide, 19.1 g (90 mmole) of potassium phosphate, 10.3 g (90 mmole) of trans-1,2-cyclohexanediamine and 1,4-dioxane 700 ml were refluxed under nitrogen for about overnight. Then, the solution was filtered at 110° C. To receive the filtrate, And the 1,4-dioxane was removed under reduced pressure from the filtrate. The filtrate was extracted with 500 ml dichloromethane and 2000 ml water, the organic layer was dried with anhydrous magnesium sulfate, the solvent was removed and the residue was purified by column chromatography on silica (hexane-ethyl acetate) to give product 8.4 g (56%).

Workup

  1. temperaturewere refluxed under nitrogen for about overnight
  2. filtrationThen, the solution was filtered at 110° C
  3. customthe 1,4-dioxane was removed under reduced pressure from the filtrate
  4. extractionThe filtrate was extracted with 500 ml dichloromethane and 2000 ml water
  5. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
  6. customthe solvent was removed
  7. customthe residue was purified by column chromatography on silica (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-8a9db235b26c47ad9e6e87a852b08f9e
Source dataset
uspto-grants-2015_03
Patent number
US08993130B2

Linked notes

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