Iodine → HCID 11118595, compound

HRID 638281Notes

Reaction equation

HRID 638281 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[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.C(Cl)Cl.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]([CH3:8])=[CH:4][CH:3]=2)[CH:16]=1

Participants

10

Reactant 5

HCID 807IodineHCID 78054-BromotolueneHCID 14798Sodium HydroxideHCID 691404-ChloroquinolineHCID 178418339Butyllithium

Product 1

HCID 11118595HCID 11118595, compoundYield 51.2%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To a solution of 4.3 g (25 mmol) of p-bromotoluene in 75 ml of ether cooled to 5° was dropwise added 15 ml of a 1.6M solution of butyl lithium in hexane, while maintaining the temperature below 5°. This mixture was stirred at 5° for 10 min. and at 30° for 10 min., and then cooled to -20°. A solution of 3.4 g (20 mmol) of 4-chloroquinoline in 15 ml of ether was added while maintaining the temperature at -20°. It was allowed to warm to room temperature during 15 min. To the reaction mixture was then added 10 ml of water and 5 g of iodine, and 60 ml of 3N sodium hydroxide. After 20 min. of stirring the organic layer was separated. The aqueous phase was extracted with an equal volume of ether in three portions. The organic phases were combined, washed with water, dried over sodium sulfate, and concentrated in vacuo to leave an oil. This oil was dissolved in methylene chloride and the solution filtered through a plug of alumina. The filtrate was concentrated in vacuo to give 2.6 g of product mp 75°-77°, as off-white needles.

Workup

  1. temperaturewhile maintaining the temperature below 5°
  2. temperaturecooled to -20°
  3. temperaturewhile maintaining the temperature at -20°
  4. stirringAfter 20 min. of stirring the organic layer
  5. customwas separated
  6. extractionThe aqueous phase was extracted with an equal volume of ether in three portions
  7. washwashed with water
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customto leave an oil
  11. filtrationthe solution filtered through a plug of alumina
  12. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f724bfbf3a804c48b387cdb709ad097f
Source dataset
uspto-grants-1985_12
Patent number
US04560692

Reaction notes

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