Phthalimide → 2-(2,2-Dimethoxypropyl)-3-fluoro-4-phthalimidonitrobenzene

HRID 2222425Notes

Reaction equation

[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[H-].[Na+].F[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[C:17]([CH2:24][C:25]([O:29][CH3:30])([O:27][CH3:28])[CH3:26])[C:16]=1[F:31]>CN(C=O)C>[CH3:30][O:29][C:25]([O:27][CH3:28])([CH3:26])[CH2:24][C:17]1[C:16]([F:31])=[C:15]([N:5]2[C:1](=[O:11])[C:2]3=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]3[C:4]2=[O:6])[CH:20]=[CH:19][C:18]=1[N+:21]([O-:23])=[O:22]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of phthalimide (4.4 g; 30 mmol) in anhydrous DMF (40 ml) cooled to 0° C. was added sodium hydride (1.29 g, 32 mmol, 60% in oil). The mixture was stirred at this temperature for 30 minutes before the addition of 1,2-difluoro-3-(2,2-dimethoxypropyl)-4-nitrobenzene (6 g, 23 mmol), (prepared as described for the starting material in Example 11). The reaction mixture was heated at 100° C. for 3 hours under argon. Upon cooling to ambient temperature, the reaction mixture was poured over ice/water (200 ml) and the formed precipitate was collected by filtration and washed with water and ether. The solid was purified by flash chromatography using methylene chloride/methanol (99/1). Evaporation of the solvent gave 2-(2,2-dimethoxypropyl)-3-fluoro-4-phthalimidonitrobenzene (5.6 g, 63%) as a yellow solid.

Workup

custom(prepared
temperatureUpon cooling to ambient temperature
filtrationthe formed precipitate was collected by filtration
washwashed with water and ether
customThe solid was purified by flash chromatography
customEvaporation of the solvent

Sources & evidence

ORD record: ord-457a9ff952d74005a9df36aa5f6c326b
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07371765B2

Reaction notes

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