Methyl iodide → 3,6-dibromo-9-methyl-9H-carbazole

HRID 1897836Notes

Reaction equation

HRID 1897836 reaction equation
Br[C:2]1SC=C2C=1NC(=O)N2.[Br:11][C:12]1[CH:13]=[CH:14][C:15]2[NH:16][C:17]3[C:22]([C:23]=2[CH:24]=1)=[CH:21][C:20]([Br:25])=[CH:19][CH:18]=3.[H-].[Na+].CI.[Cl-].[NH4+]>O.O1CCCC1>[Br:25][C:20]1[CH:19]=[CH:18][C:17]2[N:16]([CH3:2])[C:15]3[C:23]([C:22]=2[CH:21]=1)=[CH:24][C:12]([Br:11])=[CH:13][CH:14]=3

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 2748743,6-DibromocarbazoleHCID 46899383HCID 46899383, compound

Product 1

HCID 8257363,6-dibromo-9-methyl-9H-carbazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Bromo-1H-thieno[3,4-d]imidazol-2(3H)-one represented by formula (5a) was obtained in the same manner as in Example 1. In 3 ml/mmol of tetrahydrofuran to 3,6-dibromo-9H-carbazole, it was reacted with 1.1 equivalents of sodium hydride for 1 hour under argon gas atmosphere while being kept at 0° C. in an ice bath, and then 1.2 equivalents of methyl iodide was added and a reaction was further continued for 4 hours at room temperature. The reaction was stopped by adding an excessive amount of a mixed aqueous solution of ion-exchange water:ammonium chloride=3:1. The product was extracted from the resulting reaction liquid to an organic layer using diethyl ether and dried over sodium sulfate and then the solvent was evaporated, followed by a purification step by column separation using an ethyl acetate/hexane solvent, so that 3,6-dibromo-9-methyl-9H-carbazole was obtained.

Workup

  1. customwas obtained in the same manner as in Example 1
  2. customwhile being kept at 0° C. in an ice bath
  3. extractionThe product was extracted from the resulting reaction liquid to an organic layer
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was evaporated
  6. customfollowed by a purification step by column separation

Sources & evidence

ORD record
ord-9d5ad683254945d482b83100b25da6dd
Source dataset
uspto-grants-2013_08
Patent number
US08519150B2

Reaction notes

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