Propargyl bromide → 6-(Prop-2-ynyloxy)isoindolin-1-one

HRID 1727399Notes

Reaction equation

HRID 1727399 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][NH:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[CH2:12](Br)[C:13]#[CH:14].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:14]([O:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][NH:7][C:8]2=[O:11])=[CH:4][CH:3]=1)[C:13]#[CH:12]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 115283646-Hydroxy-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 575676686-(Prop-2-ynyloxy)isoindolin-1-oneYield 68.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The mixture of 6-hydroxyisoindolin-1-one ((73), 5.1 g, 34.2 mmol), propargyl bromide (80% solution in toluene, 5.70 ml, 51.3 mmol) K2CO3 (9.44 g, 68.4 mmol), KI (1.14 g, 6.8 mmol) in acetone was refluxed for overnight. The reaction mixture was filtered under vacuum and concentrated in vacuo to give the title compound (4.4 g, 68%) as a solid. MS (ES) m/z 188.1.

Workup

  1. temperaturewas refluxed for overnight
  2. filtrationThe reaction mixture was filtered under vacuum
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bcb62e825c2e4866a919ef87ce5458ec
Source dataset
uspto-grants-2009_02
Patent number
US07495111B2

Reaction notes

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