1,7-Dibromoheptane → 2-(7-Bromoheptyl)-1H-isoindole-1,3(2H)-dione

HRID 1952516Notes

Reaction equation

HRID 1952516 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][Br:9].[C:10]1(=[O:20])[NH:14][C:13](=[O:15])[C:12]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:11]12.[K]>CC(C)=O>[Br:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:14]1[C:10](=[O:20])[C:11]2[C:12](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:13]1=[O:15]

Participants

4

Reactant 2

HCID 783091,7-DibromoheptaneHCID 24194345Phthalimide potassium salt

Product 1

HCID 196989382-(7-Bromoheptyl)-1H-isoindole-1,3(2H)-dioneYield 75.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 1,7-dibromoheptane (11) (13.90 g, 53.9 mmol) in acetone (100 mL) was added potassium phthalimide (5.00 g, 27.0 mmol). The resulting mixture was refluxed for 16 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 12 as a colorless oil (6.62 g, 75%). 1H NMR (400 MHz, CDCl3) δ 7.83-7.84 (m, 2H), 7.69-7.72 (m, 2H), 3.67 (t, J=7.6 Hz, 2H), 3.39 (t, J=7.2 Hz, 2H), 1.82-1.84 (m, 2H), 1.67 (m, 2H), and 1.35 (m, 6H); 13C NMR (100 MHz, CDCl3) δ 168.55, 134.06, 132.30, 123.32, 38.06, 34.12, 32.85, 28.67, 28.48, 28.19, and 26.83.

Workup

  1. temperatureThe resulting mixture was refluxed for 16 hours
  2. customthe solvent was removed in vacuo
  3. customMPLC purification of the residue (Hexanes:EtOAc/70:30)

Sources & evidence

ORD record
ord-c8f3e3f9d8be4e56ac576c720108bf5d
Source dataset
uspto-grants-2013_03
Patent number
US08404728B2

Reaction notes

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