Hydrochloric Acid → (4-Fluorophenoxy)-2-phenylisoindol-1,3-dione

HRID 1353061Notes

Reaction equation

[N+]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:7]2=[O:20])([O-])=O.[F:21][C:22]1[CH:27]=[CH:26][C:25]([O-:28])=[CH:24][CH:23]=1.[Na+].Cl>CN(C=O)C>[F:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:11]2[CH:12]=[CH:4][CH:5]=[C:6]3[C:10]=2[C:9](=[O:13])[N:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:7]3=[O:20])=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 100 °C

Procedure

5-Nitro-2-phenylisoindole-1,3-dione (5.9 g, 22 mmol) was dissolved in DMF (40 ml) and sodium 4-fluorophenolate (3.1 g, 23.1 mmol) was added. The resulting mixture was stirred at 100° C. for 2 hours under an argon atmosphere. The mixture was allowed to cool to RT then poured into 4% aqueous HCl. The yellow precipitate which formed was filtered off, washed with water and recrystallised (DCM/TBME) to yield (4-fluorophenoxy)-2-phenylisoindol-1,3-dione (2.4 g, 41%);

Workup

temperatureto cool to RT
customThe yellow precipitate which formed
filtrationwas filtered off
washwashed with water
customrecrystallised (DCM/TBME)

Sources & evidence

ORD record: ord-70e610c15fa545eb90c52a3736970133
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220777B2

Reaction notes

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