Allyl bromide → N-Allylphthalimide

HRID 899796Notes

Reaction equation

HRID 899796 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].[CH2:13](Br)[CH:14]=[CH2:15]>CN(C=O)C>[CH2:15]([N:5]1[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[C:4]1=[O:6])[CH:14]=[CH2:13]

Participants

4

Reactant 2

HCID 7841Allyl bromideHCID 24194345Phthalimide potassium salt

Product 1

HCID 224401N-AllylphthalimideYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of potassium phthalimide (310.39 g, 1.68 mol) in DMF (1.0 L) at 0° C. was added allyl bromide (290.4 mL, 3.36 mol) from a dropping funnel over 30 minutes. The reaction was then warmed to room temperature and allowed to stir for 5 days. The mixture was filtered to remove salts while washing the residue with ethyl acetate (1 L), and the filtrate concentrated under reduced pressure. The residue was then partitioned between saturated aqueous NaHCO3 (0.5 L) and CH2Cl2 (0.8 L) and the organic phase separated. The aqueous phase was extracted with CH2Cl2 (2×0.8 L), and the combined organic phases were dried (Na2SO4), filtered and concentrated under reduced pressure to give N-allylphthalimide as a white powder (294 g, 94%). 1H NMR (CDCl3) δ 4.30 (d, 2H, J=6.0 Hz), 5.22 (m, 2H), 5.88 (m, 1H), 7.73 (m, 2H), 7.85 (m, 2H).

Workup

  1. filtrationThe mixture was filtered
  2. customto remove salts
  3. washwhile washing the residue with ethyl acetate (1 L)
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customThe residue was then partitioned between saturated aqueous NaHCO3 (0.5 L) and CH2Cl2 (0.8 L)
  6. customthe organic phase separated
  7. extractionThe aqueous phase was extracted with CH2Cl2 (2×0.8 L)
  8. dry with materialthe combined organic phases were dried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d58c216855db4653966a31084b80895f
Source dataset
uspto-grants-2008_04
Patent number
US07354934B2

Reaction notes

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