Isopropyl iodide → HCID 70984179, compound

HRID 338875Notes

Reaction equation

HRID 338875 reaction equation
[Br:1][C:2]1[C:11]([OH:12])=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH3:13])=[N:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].I[CH:21]([CH3:23])[CH3:22].C(OCC)(=O)C>CC(C)=O.O>[Br:1][C:2]1[C:11]([O:12][CH:21]([CH3:23])[CH3:22])=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH3:13])=[N:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6362Isopropyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 21824657HCID 21824657, compound

Product 1

HCID 70984179HCID 70984179, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 7-bromo-2-methylquinolin-8-ol (1.00 g, 4.20 mmol), K2CO3 (1.74 g, 12.6 mmol), and 2-iodopropane (0.84 ml, 8.40 mmol) in acetone (20 mL) was stirred at 88° C. in a seal tube for 24 hours. After cooling to ambient temperature, ethyl acetate (50 mL) and water (30 mL) was added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (5:1 hexane/ethyl acetate) to give 7-bromo-8-isopropoxy-2-methylquinoline (1.13 g, 96.0%) as an oil.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (5:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-6ac17ca26272419cb341555d7002d19e
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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