Iodine → 1-Chloro-7-iodoisoquinoline

HRID 1896882Notes

Reaction equation

HRID 1896882 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[Cl:12])=[CH:4][CH:3]=1.[Li]CCCC.[I:18]I.[O-]S([O-])(=S)=O.[Na+].[Na+]>C1COCC1>[Cl:12][C:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([I:18])[CH:11]=2)[CH:6]=[CH:7][N:8]=1

Participants

6

Reactant 4

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 65020247-Bromo-1-ChloroisoquinolineHCID 178418339Butyllithium

Product 1

HCID 441563091-Chloro-7-iodoisoquinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 7-bromo-1-chloroisoquinoline (15 g, 62 mmol) in THF at −78° C., n-BuLi (123.7 mmol) was added. The resulting solution was stirred for 15 min. and, I2 (31.4 mg, 123.7 mmol) in THF was slowly added by syringe over a period of 5 min. The solution was then allowed to reach room temperature and treated with a saturated aqueous Na2S2O3 solution. The resulting mixture was extracted with diethyl ether (2×). The extracted organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuum. The residue was purified by flash chromatography to give the title compound.

Workup

  1. customto reach room temperature
  2. extractionThe resulting mixture was extracted with diethyl ether (2×)
  3. washThe extracted organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuum
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-8693a4490e4447dea79b5db62924f505
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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