Water → 2-(2-Bromoethoxy)carbazole

HRID 2299562Notes

Reaction equation

HRID 2299562 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[NH:5][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Br:21][CH2:22][CH2:23]Br.O>CC(=O)CC>[Br:21][CH2:22][CH2:23][O:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[NH:5][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 935512-Hydroxycarbazole

Product 1

HCID 183805042-(2-Bromoethoxy)carbazole

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2-hydroxycarbazole (30 g; mfd. by Aldrich), potassium carbonate (113.1 g; mfd. by KANTO CHEMICAL) and 1,2-dibromoethane (211 mL; mfd. by TOKYO KASEI KOGYO) in 2-butanone (165 mL; mfd. by Wako Pure Chemical Industries) was stirred vigorously at a reflux temperature for 28 hours. The reaction solution was poured into water (1050 mL) all at once and stirred. The precipitated crystal obtained by filtration was washed with water (1 L) and 2-propanol (250 mL), and then dried under reduced pressure at room temperature to give the title compound (43.43 g) as a white solid.

Workup

  1. stirringstirred
  2. customThe precipitated crystal obtained by filtration
  3. washwas washed with water (1 L) and 2-propanol (250 mL)
  4. customdried under reduced pressure at room temperature

Sources & evidence

ORD record
ord-d3a78f0af721404fb8b79dcd05df3341
Source dataset
uspto-grants-2002_12
Patent number
US06495701B1

Reaction notes

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