Isopropyl iodide → HCID 86723819, compound

HRID 577590Notes

Reaction equation

HRID 577590 reaction equation
[Cl:1][C:2]1[C:3]([OH:12])=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2.I[CH:14]([CH3:16])[CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:1][C:2]1[C:3]([O:12][CH:14]([CH3:16])[CH3:15])=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 768469827-Chloro-2,3-dihydro-6-hydroxy-1H-isoindol-1-one

Product 1

HCID 86723819HCID 86723819, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 7-chloro-6-hydroxy-2,3-dihydro-isoindol-1-one (500 mg, 2.72 mmol), 2-iodopropane (556 mg, 3.27 mmol), and cesium carbonate (1.33 mg, 4.08 mmol) in DMF (20 mL) was stirred at 80° C. overnight. The solution was cooled to room temperature and the reaction mixture partitioned between ethyl acetate (50 mL) and water (50 mL). The organic phase was separated, washed with water (50 mL) and brine (50 mL), dried over sodium sulfate and concentrated under vacuum. The residue was purified by column chromatography (silica gel, heptanes/EtOAc) to give 7-chloro-6-isopropoxy-2,3-dihydro-isoindol-1-one (133a, 300 mg, 65% yield) as a solid.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. customthe reaction mixture partitioned between ethyl acetate (50 mL) and water (50 mL)
  3. customThe organic phase was separated
  4. washwashed with water (50 mL) and brine (50 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by column chromatography (silica gel, heptanes/EtOAc)

Sources & evidence

ORD record
ord-3bf1503b3d4c4573b7b0b191d1f0b44f
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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