Reaction #531871

Reaction equation

trans-2-(4-Hydroxy-cyclohexyl)-isoindole-1,3-dione

triphenylphosphine

4-fluorophenol

diisopropyl azodicarboxylate

→

cis-2-[4-(4-Fluoro-phenoxy)-cyclohexyl]isoindole-1,3-dione

Solvents

THF

Conditions

Workup

1. 1
   OtherThe solvent was evaporated after 12 h
2. 2
   Otherthe resulting solid was purified by recrystallization from methanol

Procedure

To a solution of trans-2-(4-Hydroxy-cyclohexyl)-isoindole-1,3-dione 3 (1.0 g, 4.1 mmol), triphenylphosphine (1.3 g, 4.9 mmol), and 4-fluorophenol (0.55 g, 4.9 mmol) in 40 mL of THF was added dropwise at room temperature diisopropyl azodicarboxylate (0.99 g, 4.9 mmol). The reaction mixture was stirred overnight. The solvent was evaporated after 12 h, and the resulting solid was purified by recrystallization from methanol. Yield: 1.1 g (80% of theory). 1H NMR (300 MHz, CDCl3): δ 7.84-7.80 (m, 2H), 7.71-7.67 (m, 2H), 6.98-6.94 (m, 4H), 4.51 (s, 1H), 4.26-4.12 (m, 1H), 2.76-2.60 (m, 2H), 2.18 (d, J=13 Hz, 2H), 1.79-1.49 (m, 4H).

Source