Carbon Tetrachloride → 3-Bromo-6-chloroquinoline

HRID 1297530Notes

Reaction equation

HRID 1297530 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-511fd4dc2b1248bf86c7fb8b1ddca66f
Source dataset
uspto-grants-2007_07
Patent number
US07250516B2

Reaction notes

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