Tetrafluorophthalic anhydride → (R)-2-(1-phenylethyl)-4,5,6,7-tetrafluoro-1H-isoindole-1,3-dione

HRID 1058072Notes

Reaction equation

[F:1][C:2]1[C:3]([F:15])=[C:4]([F:14])[C:5]([F:13])=[C:6]2[C:11](=[O:12])[O:10][C:8](=O)[C:7]=12.[CH3:16][C@@H:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)(Cl)Cl>[C:18]1([C@H:17]([N:24]2[C:11](=[O:12])[C:6]3[C:7](=[C:2]([F:1])[C:3]([F:15])=[C:4]([F:14])[C:5]=3[F:13])[C:8]2=[O:10])[CH3:16])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 180 °C

Procedure

220 mg of tetrafluorophthalic anhydride and 121 mg of (R)-α-methylbenzylamine were charged in an egg-plant type flask of 50 ml, followed by stirring under heating at a temperature of 180° C. for 2 hours. After cooled, the reaction product was dissolved in chloroform, purified by silica gel column chromatography (eluent; methylene k chloride:methanol=30:1 v/v), recrystallized from a mixed solvent of n-hexane-ethyl acetate, to obtain 210 mg of the desired product as colorless needles. Yield: 65%. m.p. 95.5-96° C.; [α]20 D=41.5° (C=0.348 AcOEt); MS(EI+) 323 (M)+

Workup

temperatureAfter cooled
custompurified by silica gel column chromatography (eluent; methylene k chloride:methanol=30:1 v/v)
customrecrystallized from a mixed solvent of n-hexane-ethyl acetate

Sources & evidence

ORD record: ord-25047d0b35f74f4ea6741da74ae3177d
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06515129B1

Reaction notes

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