Carbazole → HCID 57983707, compound

HRID 1868531Notes

Reaction equation

HRID 1868531 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[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.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CNCCNC>C(Cl)Cl.[Cu](I)I.O1CCOCC1>[CH3:11][O:10][C:4]1[CH:3]=[C:2]([N:23]2[C:24]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[C:17]3[C:22]2=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=1

Participants

8

Reactant 4

HCID 6854CarbazoleHCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 6391871-Bromo-3,5-dimethoxybenzene

Product 1

HCID 57983707HCID 57983707, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

To a three neck round bottom flask, was charged bromo-3,5-dimethoxybenzene (1.54 g, 7.1 mmol), carbazole (1.186 g, 7.1 mmol), potassium phosphate (3 g, 14.2 mmol) and copper iodide (0.14 g, 0.7 mmol). Dioxane (40 ml) was added and the reaction flask. The flask was evacuated and flushed with argon. Dimethylethylene diamine (0.14 g, 1.6 mmol) was then added to the reaction flask under a strong purge of argon. The reaction mixture was then heated at 95° C. for 48 h under argon. The reaction was followed by TLC. After the reaction was complete, the solution was cooled down to room temperature, and 10 mL of H2O was added. The reaction mixture was extracted with methylene chloride and the organic and aqueous phases were separated. The organic phase was further washed twice with 100 mL of water (×2) and once with 100 mL of brine (×1) and dried over Na2SO4. After solvent removal under vacuo, afforded crude product. Crude product was dissolved in CH2Cl2 and hexanes were added until the colored residues precipitated out. The solution was filtered to remove the colored residues. The mother liquor was concentrated to afford 1.0 g (46.5%) of light yellow oil as the product. 1H NMR (CDCl3) δ 7.98 (d, 2H), 7.35 (d, 2H), 7.23 (d, 2H), 7.11 (t, 2H), 6.6 (s, 2H), 6.43 (s, 1H), 3.65 (s, 6H). EI-MS: 303(M+).

Workup

  1. customThe flask was evacuated
  2. customflushed with argon
  3. customa strong purge of argon
  4. temperaturethe solution was cooled down to room temperature
  5. addition10 mL of H2O was added
  6. extractionThe reaction mixture was extracted with methylene chloride
  7. customthe organic and aqueous phases were separated
  8. washThe organic phase was further washed twice with 100 mL of water (×2) and once with 100 mL of brine (×1)
  9. dry with materialdried over Na2SO4
  10. customAfter solvent removal under vacuo
  11. customafforded crude product
  12. customprecipitated out
  13. filtrationThe solution was filtered
  14. customto remove the colored residues
  15. concentrationThe mother liquor was concentrated
  16. customto afford 1.0 g (46.5%) of light yellow oil as the product

Sources & evidence

ORD record
ord-430a727dbb164d6cbff2282e9e8cab66
Source dataset
uspto-grants-2009_12
Patent number
US07635777B2

Reaction notes

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