1,3-Isobenzofurandione, 5-fluoro- → 2-(3-Bromo-2-methylphenyl)-5-fluoroisoindoline-1,3-dione

HRID 1811006

Reaction equation

[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[F:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[C:16](=[O:20])[O:15][C:14]2=O>C(O)(=O)C>[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([N:5]2[C:14](=[O:15])[C:13]3[C:17](=[CH:18][CH:19]=[C:11]([F:10])[CH:12]=3)[C:16]2=[O:20])[CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-bromo-2-methylaniline (200 mg, 1.075 mmol) and 5-fluoroisobenzofuran-1,3-dione (179 mg, 1.075 mmol) in acetic acid (2 mL) was heated at 100° C. for 4.5 h. The mixture was concentrated and the residue was purified by column chromatography (eluting with a gradient from hexane to 60:40 hexane-EtOAc) to give 2-(3-bromo-2-methylphenyl)-5-fluoroisoindoline-1,3-dione as a white solid (235 mg, 59%). Mass spectrum m/z 334, 336 (M+H)+.

Workup

concentrationThe mixture was concentrated
customthe residue was purified by column chromatography (
washeluting with a gradient from hexane to 60:40 hexane-EtOAc)

Sources & evidence

ORD record: ord-f04cdbdad9294dd4ae86f355737253ae
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362065B2

Linked notes

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