Carbazole → 9-hexylcarbazole

HRID 1638233Notes

Reaction equation

HRID 1638233 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-].[K+].[CH2:16](Br)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>O>[CH2:16]([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)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 6854CarbazoleHCID 81011-BromohexaneHCID 14797Potassium Hydroxide

Product 1

HCID 41256079-hexylcarbazoleYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

Carbazole (23.66 g, 0.16 mol), potassium hydroxide (14.45 g. 0.226 mol), water (30 g) and line (100 g) were added into a 500 ml four neck flask equipped with Dean-stark apparatus, and refluxed. Water (about 30 g) was separated, and the reaction mixture was cooled to 90 to 100° C. Hexyl bromide (33 g, 0.2 mol) was added dropwise thereto over about 25 minutes, and then reflux was carried out for 1 hour. 9-hexylcarbazole was obtained in a 95% yield.

Workup

  1. customequipped with Dean-stark apparatus
  2. temperaturerefluxed
  3. customWater (about 30 g) was separated
  4. temperaturereflux
  5. waitwas carried out for 1 hour

Sources & evidence

ORD record
ord-18a2f33d407e4b54a9d8a5a74a4d8073
Source dataset
uspto-grants-2000_03
Patent number
US06043428

Reaction notes

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