N-Iodosuccinimide → 8-Bromo-3-iodoquinoline

HRID 2241986Notes

Reaction equation

HRID 2241986 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[I:12]N1C(=O)CCC1=O>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([I:12])=[CH:7]2

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 1401098-Bromoquinoline

Product 1

HCID 529878958-Bromo-3-iodoquinoline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 8-bromoquinoline (commercially available, 1.0 g) in glacial acetic acid (6 mL) was added portionwise, N-iodosuccinimide (1.08 g). The resulting mixture was stirred at 70° C. for 18 hours. The reaction was cooled to room temperature and concentrated on a rotary evaporator. The residue was taken up in CH2Cl2 and washed with saturated aqueous NaHCO3 and brine. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated on a rotary evaporator. The crude product was purified by flash chromatography on silica using hexane/ethyl acetate to give 0.74 g of the desired product as a white solid; MS (ES) m/z (relative intensity): 334 (M+H)+ (100).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated on a rotary evaporator
  3. washwashed with saturated aqueous NaHCO3 and brine
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated on a rotary evaporator
  7. customThe crude product was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-77379370eaa9426dae2f79c19c0c4da0
Source dataset
uspto-grants-2010_03
Patent number
US07671056B2

Reaction notes

Loading…