Carbazole → N-Benzylcarbazole

HRID 659613Notes

Reaction equation

HRID 659613 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.[H-].[Na+].Br[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CCOC(C)=O>CN(C=O)C>[CH2:17]([N:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 6854CarbazoleHCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 24758Sodium hydride

Product 1

HCID 146485N-BenzylcarbazoleYield 90.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 100-mL round-bottomed flask was charged with a solution of 9H-carbazole (1.67 g, 9.90 mmol, 1.00 equiv, 99%) in DMF (20 mL) followed by addition of NaH (400 mg, 16.50 mmol, 1.00 equiv, 99%) in small portions at 0° C. over 5 minutes. 1-(Bromomethyl)benzene (1.7 g, 9.90 mmol, 1.00 equiv, 99%) was then added drop wise at 0° C. over 5 minutes. The resulting mixture was stirred at room temperature for 16 hours. The progress was monitored by TLC (EtOAc:PE=1:5). Upon completion, the reaction was then quenched by the addition of water/ice (100 mL). The solids were collected by filtration and dried in an oven under reduced pressure to afford 9-benzyl-9H-carbazole as white solid (2.3 g, 90%). LCMS: [M+H]+: 258.

Workup

  1. customUpon completion, the reaction was then quenched by the addition of water/ice (100 mL)
  2. filtrationThe solids were collected by filtration
  3. customdried in an oven under reduced pressure

Sources & evidence

ORD record
ord-c58f6de1c7b3428f9031ff6318a9c828
Source dataset
uspto-grants-2011_12
Patent number
US08080566B1

Reaction notes

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