Carbazole → HCID 178478525, compound

HRID 1838513Notes

Reaction equation

HRID 1838513 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.[CH2:14]([Li])[CH2:15][CH2:16][CH3:17].[Cl-:19].[Cl-].[Cl-].[Cl-].[Zr+4:23]>C1(C)C=CC=CC=1>[Cl-:19].[Cl-:19].[C:10]1([Zr+2:23][C:17]2[C:13]3[NH:12][C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:5]=3[CH:14]=[CH:15][CH:16]=2)[C:11]2[NH:12][C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6854Carbazole2×HCID 9856075Zirconium chloride (ZrCl4), (T-4)-HCID 178418339Butyllithium

Product 1

HCID 178478525HCID 178478525, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Complex Preparation (Steps 1 and 2). Carbazole (5.0 g, 30 mmol) is stirred in a flask under an atmosphere of nitrogen in a dry box for 15 min. Toluene (120 mL) is added, and the mixture is stirred for 30 min. n-Butyllithium (12 mL of 2.5 M solution in hexane, 30 mmol) is added by syringe over 5 min. to the stirred carbazole solution. The mixture is stirred at room temperature for 2 h. The mixture turns light pink, and the slurry becomes thick, requiring vigorous stirring. Zirconium tetrachloride (3.50 g, 15 mmol) and more toluene (25 mL) are added to the flask, and the mixture turns brown. Stirring is continued at room temperature for another 18 h, after which the mixture is black-brown-green. Solvents are removed under a flow of nitrogen, and the residue is vacuum dried for 3 h. A yellow solid (9.25 g) that contains 81 wt. % of the desired bis(carbazolyl) complex (15.1 wt. % Zr) is isolated.

Workup

  1. customComplex Preparation (Steps 1 and 2)
  2. stirringStirring
  3. waitis continued at room temperature for another 18 h
  4. customSolvents are removed under a flow of nitrogen
  5. customdried for 3 h
  6. customis isolated

Sources & evidence

ORD record
ord-8be2faf9418c4a97b3fcbed062578821
Source dataset
uspto-grants-2004_01
Patent number
US06673882B2

Reaction notes

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