Allyl bromide → N-Allyloxyphthalimide

HRID 982655Notes

Reaction equation

HRID 982655 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].[CH2:13]1[CH2:23]CN2C(=NCCC2)C[CH2:14]1.C(Br)C=C>CN(C=O)C>[CH2:23]([O:1][N:2]1[C:3](=[O:12])[C:4]2=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]2[C:6]1=[O:7])[CH:13]=[CH2:14]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 10665N-HydroxyphthalimideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 2765097N-AllyloxyphthalimideYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled solution (5 to 10° C.) of N-hydroxyphthalimide (53.80 g, 0.33 mol) in DMF (120 mL), was added DBU (46.36 mL, 0.31 mol) was added in one portion, with stirring. After 10 minutes, allyl bromide (25.96 mL, 0.30 mol) was added in portions. The cooling bath was removed and the reaction mixture was stirred at room temperature for 1 hour, until the color turned from dark burgundy to yellow. Ethyl acetate (300 mL) and water (150 mL) were added, the aqueous phase was separated, and the organic phase was washed with water (4×50 mL). The combined aqueous extracts were back-extracted with EtOAc (3×50 mL) and the total EtOAc solution was washed with saturated NaHCO3 (10×50 mL) until the aqueous phase was pale yellow, then with brine (2×75 mL) and dried over anhydrous MgSO4. Removal of the solvent afforded 58.83 g (96% yield) of the product as a white solid.

Workup

  1. additionwas added in one portion
  2. customThe cooling bath was removed
  3. stirringthe reaction mixture was stirred at room temperature for 1 hour, until the color
  4. additionEthyl acetate (300 mL) and water (150 mL) were added
  5. customthe aqueous phase was separated
  6. washthe organic phase was washed with water (4×50 mL)
  7. extractionThe combined aqueous extracts were back-extracted with EtOAc (3×50 mL)
  8. washthe total EtOAc solution was washed with saturated NaHCO3 (10×50 mL) until the aqueous phase
  9. dry with materialwith brine (2×75 mL) and dried over anhydrous MgSO4
  10. customRemoval of the solvent

Sources & evidence

ORD record
ord-41450e21f5c544799f1ccbe86457a847
Source dataset
uspto-grants-2005_03
Patent number
US06861416B2

Reaction notes

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