Ethyl Acetate → 5-Fluoro-1-(4-fluorophenyl)indoline-2,3-dione

Participants

Reaction Steps

Oxalyl chloride (9.62 ml, 0.11 mole) was dissolved in 45 ml CH2Cl2. A solution of di-(4-fluorophenyl)amine (19.7 g, 0.096 mole) in 145 ml CH2Cl2 was added over 15 minutes; the temperature rose from 23° to 28°. After stirring 1 hour, AlCl3 (40.8 g) was added portionwise over 15 minutes; the temperature rose from 20° to 30°, and was kept less than 30° by cooling. After stirring for 10 minutes, the reaction mixture was added to 250 ml ethyl acetate and 500 ml ice and water (the temperature rose to 30° C.). The aqueous layer was washed 2×250 ml ethyl acetate. The organic layers were combined, back-washed 1×400 ml H2O, dried over MgSO4, evaporated to solids and triturated with 100 ml 1:1 ether:hexane to recover title product, 19.9 g, m.p. 180°-190°, tlc Rf 0.55 (1:1 ether:hexane).

Provenance & Evidence