Dimethylformamide → N-3-Bromopropylphthalimide

HRID 1784180Notes

Reaction equation

HRID 1784180 reaction equation
Br[C:2]([Br:5])([CH3:4])C.[C:6]1(=[O:16])[NH:10][C:9](=[O:11])[C:8]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:7]12.[K].[CH3:18]N(C=O)C>>[Br:5][CH2:2][CH2:4][CH2:18][N:10]1[C:6](=[O:16])[C:7]2[C:8](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:9]1=[O:11]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 116582,2-DibromopropaneHCID 24194345Phthalimide potassium salt

Product 1

HCID 21611N-3-BromopropylphthalimideYield 49%

Conditions

Temperature
90 °C

Procedure

To a solution of dibromopropane (0.61 mL, 6.0 mmol) in DMF (8 mL) was added potassium phthalimide (0.2756 g, 1.5 mmol), and was stirred at 90° C. for 17 hours. The mixture was concentrated, 1N NaOH (10 mL) was added, and extracted with CH2Cl2 (2×30 mL). The combined organic extracts were washed with water (1×15 mL), dried (Na2SO4), and concentrated. Purification of the crude material by column chromatography on silica gel (4:1 hexanes-EtOAc) provided 0.1977 g (49%) of 2-(3-bromo-propyl)-isoindole-1,3-dione as a white solid. 1H NMR (CDCl3) δ 2.21-2.30 (m, 2H), 3.41 (t, 2H, J=6.0 Hz), 3.83 (t, 2H, J=6.0 Hz), 7.69-7.75 (m, 2H), 7.82-7.86 (m, 2H).

Workup

  1. concentrationThe mixture was concentrated
  2. addition1N NaOH (10 mL) was added
  3. extractionextracted with CH2Cl2 (2×30 mL)
  4. washThe combined organic extracts were washed with water (1×15 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customPurification of the crude material by column chromatography on silica gel (4:1 hexanes-EtOAc)

Sources & evidence

ORD record
ord-a99bbec6227e4e2e9b0c57a1c96457cd
Source dataset
uspto-grants-2009_03
Patent number
US07501518B2

Reaction notes

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