Water → 1h-Isoindol-1-one,2,3-dihydro-5-(4-nitrophenoxy)-

HRID 598443Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[NH:6][CH2:5]2.F[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1.O>CN(C=O)C>[C:7]1(=[O:11])[C:8]2[C:4](=[CH:3][C:2]([O:1][C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=3)=[CH:10][CH:9]=2)[CH2:5][NH:6]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a slurry of Nail (0.39 g, 16.1 mmol) in DMF at 0° C. was added 5-hydroxyisoindolin-1-one (2.0 g, 13.4 mmol) in portions. The resulting slurry was allowed to warm to room temp. and was stirred for 45 min., then 4-fluoro-1-nitrobenzene was added and then mixture was heated at 70° C. for 3 h. The mixture was cooled to 0° C. and treated with water dropwise until a precipitate formed. The resulting solids were collected to give 4-(1-isoindolinon-5-yloxy)-1-nitrobenzene as a dark yellow solid (3.23 g, 89%): TLC (100% EtOAc) Rf 0.35.

Workup

temperatureto warm to room temp.
temperatureThe mixture was cooled to 0° C.
customformed
customThe resulting solids were collected

Sources & evidence

ORD record: ord-600a883e9e99464d869181a3dd1f73a1
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897623B2

Reaction notes

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