Iodine → 4-Chloro-2-(4-chlorophenyl)quinoline

HRID 638259Notes

Reaction equation

HRID 638259 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=1.C([Li])CCC.[Cl:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=[CH:17][CH:16]=1.II.[OH-].[Na+]>CCOCC.CCCCCC.O>[Cl:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=[C:17]([C:2]2[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=2)[CH:16]=1

Participants

9

Reactant 5

HCID 807IodineHCID 7806p-BromochlorobenzeneHCID 14798Sodium HydroxideHCID 691404-ChloroquinolineHCID 178418339Butyllithium

Product 1

HCID 112195464-Chloro-2-(4-chlorophenyl)quinolineYield 92%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution of 15.3 g (80 mmol) of 4-bromochlorobenzene in 100 ml of ether cooled to -25° was added 60 ml of a 1.6M solution of butyl lithium in hexane in three portions while maintaining the temperature below -20°. This mixture was allowed to warm to -5° during 15 min. It was then recooled to -20°, and a solution of 11.45 g (70 mmol) of 4-chloroquinoline in 40 ml of ether was added while maintaining the temperature at -20°. A yellow suspension formed. It was allowed to warm to 0° for 15 min, and was then stirred for a further 20 min at 0°-10°. To the reaction mixture was then added 20 ml of water and 20 g of iodine. After 20 min of stirring 40 ml of 3N sodium hydroxide solution was added and stirring was continued for a further 15 min. This mixture was then cooled to 10°, and the solid collected to give 17.65 g of product, mp 119°-122°.

Workup

  1. temperaturewhile maintaining the temperature below -20°
  2. temperatureto warm to -5° during 15 min
  3. customwas then recooled to -20°
  4. temperaturewhile maintaining the temperature at -20°
  5. customA yellow suspension formed
  6. temperatureto warm to 0° for 15 min
  7. additionwas added
  8. stirringstirring
  9. waitwas continued for a further 15 min
  10. temperatureThis mixture was then cooled to 10°
  11. customthe solid collected

Sources & evidence

ORD record
ord-ea50e2644bb9469c82edaac206d156d9
Source dataset
uspto-grants-1985_12
Patent number
US04560692

Reaction notes

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