Reaction #2389091

Reaction equation

tetrafluorophthalic anhydride

(S)-α-methylbenzylamine

→

desired product

Yield 74.4%

(S)-2-(1-phenylethyl)-4,5,6,7-tetrafluoro-1H-isoindole-1,3-dione

Yield 74.4%

Solvents

chloroform

Conditions

Workup

1. 1
   TemperatureAfter cooled
2. 2
   Otherpurified by silica gel column chromatography (eluent; methylene chloride:methanol=30:1 v/v)
3. 3
   Otherrecrystallized from a mixed solvent of n-hexane-ethyl acetate

Procedure

220 mg of tetrafluorophthalic anhydride and 121 mg of (S)-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 chloride:methanol=30:1 v/v), recrystallized from a mixed solvent of n-hexane-ethyl acetate, to obtain 240 mg of the desired product as colorless needles. Yield: 74%. m.p. 95-96° C.; [α]20D=−42.2° (C=0.386 AcOEt); MS(EI+) 323(M)+

Source