1,6-Dibromohexane → N-(6-Bromohexyl)phthalimide

HRID 1952496Notes

Reaction equation

HRID 1952496 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][Br:8].[C:9]1(=[O:19])[NH:13][C:12](=[O:14])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]12.[K]>CC(C)=O>[Br:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:13]1[C:9](=[O:19])[C:10]2[C:11](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:12]1=[O:14]

Participants

4

Reactant 2

HCID 123681,6-DibromohexaneHCID 24194345Phthalimide potassium salt

Product 1

HCID 141120N-(6-Bromohexyl)phthalimideYield 75.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 1,6-dibromohexane (9) (16.5 g, 67.5 mmol) in acetone (100 mL) was added potassium phthalimide (5.00 g, 27.0 mmol). The resulting mixture was refluxed for 24 hours. The reaction mixture was cooled to room temperature and the solvent was removed in vacuo. MPLC purification of the residue (Hexanes:EtOAc/70:30) gave 10 as a colorless oily liquid (6.3 g, 75%). 1H NMR (400 MHz, CDCl3) δ 7.85-7.83 (m, 2H), 7.72-7.70 (m, 2H), 3.68 (t, J=7.2 Hz, 2H), 3.39 (t, J=6.8 Hz, 2H), 1.89-1.82 (m, 2H), 1.73-1.66 (m, 2H), 1.52-1.45 (m, 2H), and 1.41-1.33 (m, 2H).

Workup

  1. temperatureThe resulting mixture was refluxed for 24 hours
  2. customthe solvent was removed in vacuo
  3. customMPLC purification of the residue (Hexanes:EtOAc/70:30)

Sources & evidence

ORD record
ord-4bca8566fc5b40988fd1f34881de73e3
Source dataset
uspto-grants-2013_03
Patent number
US08404728B2

Reaction notes

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