Allyl bromide → HCID 15018887, compound

HRID 1709107Notes

Reaction equation

HRID 1709107 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[CH:8]=[CH2:9].[OH:11][C:12]1[CH:13]=[C:14]([N:18]2[C:22](=[O:23])[C:21]3[CH2:24][CH2:25][CH2:26][CH2:27][C:20]=3[C:19]2=[O:28])[CH:15]=[CH:16][CH:17]=1>CC(C)=O>[CH2:7]([O:11][C:12]1[CH:13]=[C:14]([N:18]2[C:19](=[O:28])[C:20]3[CH2:27][CH2:26][CH2:25][CH2:24][C:21]=3[C:22]2=[O:23])[CH:15]=[CH:16][CH:17]=1)[CH:8]=[CH2:9]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 127692364,5,6,7-Tetrahydro-2-(3-hydroxyphenyl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 15018887HCID 15018887, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3.0 g of powdered potassium carbonate, then 2.6 g of allyl bromide were added to a stirred suspension of 5.0 g of 1A in 25 mL of acetone. The mixture was refluxed for 1 hour, then stirred overnight at room temperature. The solvent was evaporated, water was added to the residue and the pH of the mixture was adjusted to 11 by addition of 10% aqueous sodium hydroxide. The resulting mixture was extracted with ethyl acetate, the extract was washed with brine and dried (Na2SO4), the solvent was evaporated and the residue was flash chromatographed on silica gel with a 1:9 v:v mixture of ethyl acetate and hexane as eluent to give N-(3-allyloxyphenyl)-3,4,5,6-tetrahydrophthalimide (1B), as yellow crystals, m.p.: 88°-90° C.

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. customThe solvent was evaporated
  3. additionwater was added to the residue
  4. additionthe pH of the mixture was adjusted to 11 by addition of 10% aqueous sodium hydroxide
  5. extractionThe resulting mixture was extracted with ethyl acetate
  6. washthe extract was washed with brine
  7. dry with materialdried (Na2SO4)
  8. customthe solvent was evaporated
  9. customchromatographed on silica gel with a 1:9 v
  10. additionv mixture of ethyl acetate and hexane as eluent

Sources & evidence

ORD record
ord-bd79cca8ea444566962cd5add55e75e2
Source dataset
uspto-grants-1990_08
Patent number
US04948418

Reaction notes

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