Water → 9-Allylcarbazole

HRID 1907070Notes

Reaction equation

HRID 1907070 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.[OH-].[Na+].[CH2:16](Br)[CH:17]=[CH2:18].O>CS(C)=O>[CH2:18]([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)[CH:17]=[CH2:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6854CarbazoleHCID 7841Allyl bromideHCID 14798Sodium Hydroxide

Product 1

HCID 30903939-Allylcarbazole

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 10.85 g (65.0 mmol) of carbazole, 2.60 g (65.0 mmol) of sodium hydroxide and 6.1 mL (72.0 mmol) of allylbromide in 100 mL dimethylsulfoxide was heated to 60° C. for 5 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and then concentrated. The crude product was purified using column chromatography (silica, 1:4 dichloromethane:hexane). Yield: 9.85 g (73%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. concentrationconcentrated
  4. customThe crude product was purified

Sources & evidence

ORD record
ord-8924992a12674449adcdf271cc643393
Source dataset
uspto-grants-2013_12
Patent number
US08597803B2

Reaction notes

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