Pentanochlor → 3,6-dibromo-9-((oxiran-2-yl)methyl)-9H-carbazole

HRID 555312Notes

Reaction equation

HRID 555312 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][C:10]([Br:15])=[CH:9][CH:8]=3.CC[CH2:18][CH:19]([C:21](NC1C=CC(C)=C(Cl)C=1)=[O:22])C>C1(C)C=CC=CC=1>[Br:15][C:10]1[CH:9]=[CH:8][C:7]2[N:6]([CH2:18][CH:19]3[CH2:21][O:22]3)[C:5]3[C:13]([C:12]=2[CH:11]=1)=[CH:14][C:2]([Br:1])=[CH:3][CH:4]=3

Participants

4

Reactant 2

HCID 16826PentanochlorHCID 2748743,6-Dibromocarbazole

Product 1

HCID 27754733,6-dibromo-9-((oxiran-2-yl)methyl)-9H-carbazoleYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

At rt under an inert atmosphere, (±)-glycyclol (0.129 g, 1.74 mmol, 120 uL) is added into a solution of 3,6-dibromo-9-H-carbazole (0.565 g, 1.74 mmol) in anhydrous toluene (10 mL). Then CMMP (which is prepared according to the protocol of Tetsuto, Tsunoda Tett. Lett. 1996, 37(14), 2459-2462) (0.20 g, 1.74 mmol) is added. The resulting mixture is allowed to stir at rt for 16 hours. The solvent is evaporated and the crude compound is purified via flash chromatography using Biotage device and Petroleum Ether/DCM (3/1) as eluant to give the title compound in a 60% yield as a white solid and 5% of (±)-3,6-dibromo-9-[(1E)-3-(3,6-dibromocarabazol-9-yl)propen-1-enyl]carbazole as a grey powder.

Workup

  1. addition1996, 37(14), 2459-2462) (0.20 g, 1.74 mmol) is added
  2. customThe solvent is evaporated
  3. customthe crude compound is purified via flash chromatography

Sources & evidence

ORD record
ord-925c7a70393742c09029a372f624778c
Source dataset
uspto-grants-2011_11
Patent number
US08053436B1

Reaction notes

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