1,7-Dibromoheptane → 2-(7-Bromoheptyl)-1H-isoindole-1,3(2H)-dione
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
Product 1
Reagents, catalysts & solvents 1
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.