Allyl bromide → HCID 19800641, compound

HRID 1646440Notes

Reaction equation

HRID 1646440 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:19])[N:5]([C:12]([CH:16]([CH3:18])[CH3:17])([CH3:15])[C:13]#[N:14])[C:6]2=[O:11].C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[CH:27]=[CH2:28]>CC(C)=O>[CH2:28]([O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:19])[N:5]([C:12]([CH:16]([CH3:17])[CH3:18])([CH3:15])[C:13]#[N:14])[C:6]2=[O:11])[CH:27]=[CH2:26]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 19800633HCID 19800633, compound

Product 1

HCID 19800641HCID 19800641, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-hydroxy-α-isopropyl-α-methyl-1,3-dioxo-2-isoindolineacetonitrile (25.5 g, 0.099 mol), potassium carbonate (75.0 g, 0.543 mol) and acetone is stirred for 4 hours at reflux temperature under a nitrogen atmosphere, cooled to room temperature and treated with allyl bromide (34.1 mL, 0.395 mol). The reaction mixture is stirred overnight at reflux temperature, cooled to room temperature and filtered. The filtrate is concentrated in vacuo, diluted with ether, washed with brine, dried (MgSO4) and concentrated in vacuo to afford the title product as a yellow-orange semi-solid, 26.9 g (91.5% crude yield). The sample is purified by flash chromatography (silica gel, CH2Cl2) to afford a colorless solid, mp 54°-58° C.

Workup

  1. temperatureat reflux temperature under a nitrogen atmosphere
  2. stirringThe reaction mixture is stirred overnight
  3. temperatureat reflux temperature
  4. temperaturecooled to room temperature
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated in vacuo
  7. additiondiluted with ether
  8. washwashed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7972a78d83184c47b2f6bd3bc4c6fdec
Source dataset
uspto-grants-1993_01
Patent number
US05180419

Reaction notes

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