Carbon Tetrachloride → 3-Bromo-6-chloroquinoline

HRID 1363469Notes

Reaction equation

HRID 1363469 reaction equation
[Br:1]Br.C(Cl)(Cl)(Cl)Cl.[Cl:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][CH:13]=[CH:12]2>N1C=CC=CC=1>[Br:1][C:13]1[CH:14]=[N:15][C:16]2[C:11]([CH:12]=1)=[CH:10][C:9]([Cl:8])=[CH:18][CH:17]=2

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 24408BromineHCID 691636-Chloroquinoline

Product 1

HCID 153784653-Bromo-6-chloroquinoline

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

The synthesis was done by the same procedure as that of J. J. Eisch (J. Org. Chem. Vol. 27, p. 1318, 1962). Bromine (79 μl) and carbon tetrachloride (2 ml) were added to 6-chloroquinoline (250 mg) and stirred at 90° C. for two hours. Pyridine (123 μl) was added to the reaction solution and stirred at the same temperature for 16 hours. The reaction solution was concentrated and purified with a silica gel chromatography (hexane-ethyl acetate) to obtain the title compound (250 mg).

Workup

  1. stirringstirred at the same temperature for 16 hours
  2. concentrationThe reaction solution was concentrated
  3. custompurified with a silica gel chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-7813765e46f74506a2ddf1c1952f7ddd
Source dataset
uspto-grants-2011_02
Patent number
US07884204B2

Reaction notes

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