Isopropyl iodide → HCID 15453525, compound

HRID 2228652Notes

Reaction equation

HRID 2228652 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[CH:8]([CH3:10])[CH3:9].[F:11][C:12]1[CH:13]=[CH:14][C:15]([OH:32])=[C:16]([CH:31]=1)[O:17][CH2:18][CH2:19][N:20]1[C:28](=[O:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]1=[O:30]>C(#N)C>[F:11][C:12]1[CH:13]=[CH:14][C:15]([O:32][CH:8]([CH3:10])[CH3:9])=[C:16]([CH:31]=1)[O:17][CH2:18][CH2:19][N:20]1[C:21](=[O:30])[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:28]1=[O:29]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 15453519HCID 15453519, compound

Product 1

HCID 15453525HCID 15453525, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

7.71 g of potassium carbonate (56 mmol) and 7 ml of 2-iodopropane (70 mmol) are added to a solution of 14 g of 2-[2-(5-fluoro-2-hydroxyphenoxy)ethyl]isoindole-1,3-dione (6) (47 mmol) in 250 ml of acetonitrile. The mixture is stirred for 16 hours at 80° C. and the solvent is then evaporated off under reduced pressure and the residue is taken up in diethyl ether. The organic phase is washed with normal aqueous sodium hydroxide solution and then with saturated aqueous sodium chloride solution. It is dried over magnesium sulfate and filtered, and the solvent is evaporated off under vacuum. The title product is isolated by chromatography on a column of silica (eluent: 82/18 cyclohexane/ethyl acetate). 12.2 g of a white solid are isolated.

Workup

  1. customthe solvent is then evaporated off under reduced pressure
  2. washThe organic phase is washed with normal aqueous sodium hydroxide solution
  3. dry with materialIt is dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-25b389bf2b27422ea72d33ae4f7c48bb
Source dataset
uspto-grants-2002_07
Patent number
US06417222B1

Reaction notes

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