Potassium phthalamide → 2-{[3-Bromo-2-(methyloxy)phenyl]methyl}-1H-isoindole-1,3(2H)-dione

HRID 564459Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8]Br)[C:3]=1[O:10][CH3:11].[C:12]([NH2:23])(=[O:22])[C:13]1[C:14](=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:15](N)=[O:16].[K]>CN(C=O)C>[Br:1][C:2]1[C:3]([O:10][CH3:11])=[C:4]([CH2:8][N:23]2[C:12](=[O:22])[C:13]3[C:14](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:15]2=[O:16])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 1-bromo-3-(bromomethyl)-2-(methyloxy)benzene (41.4 g, 0.15 mol) in DMF (350 mL), Potassium Phthalamide (PhtK) (28.8 g, 0.16 mol) was added, and the mixture was heated to 90° C. over night. Then the solvent was removed under reduced pressure. The residue was dissolved in CHCl3 (300 mL), and filtered. The filtrate was washed with H2O (100 mL×2), brine (100 mL), and dried over Na2SO4. After removing the solvent, the residue was recrystallized with EtOH (200 mL). 26.7 g of the product was obtained as white solid. Yield: 52.1%. 1H NMR (400 MHz, CDCl3) δ 3.98 (s, 3 H), 4.95 (s, 2H), 6.93 (t, J=8.0 Hz, 1 H), 7.20 (d, J=0.8 Hz, 1 H), 7.45 (d, J=8.0 Hz, 1 H), 7.72-7.87 (m, 4 H).

Workup

customThen the solvent was removed under reduced pressure
dissolutionThe residue was dissolved in CHCl3 (300 mL)
filtrationfiltered
washThe filtrate was washed with H2O (100 mL×2), brine (100 mL)
dry with materialdried over Na2SO4
customAfter removing the solvent
customthe residue was recrystallized with EtOH (200 mL)

Sources & evidence

ORD record: ord-2e3ba3d52156483ebe63a8bab847b8f6
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067408B2

Reaction notes

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