Phthalimide → 2-[1-(4-Bromo-phenyl)-ethyl]-isoindole-1,3-dione

Participants

Reaction Steps

To a solution of 4-bromo-α-methylbenzylalcohol (3.0 g, 0.015 mol), phthalimide (2.2 g, 0.015 mol) and triphenylphosphine (6.0 g, 0.023 mol) in tetrahydrofuran was added diethyl azodicarboxylate (4.0 g, 0.023 mol) and the reaction mixture was stirred at room temperature for 14 hours. The solution was concentrated and the crude material was purified on silica gel (10˜35% ethyl acetate in hexane) to give 2.93 g of the title compound (60% yield) 1H NMR (300 MHz, CDCl3) δ ppm 1.90 (d, J=7.35 Hz, 3 H) 5.52 (q, J=7.11 Hz, 1 H) 7.34-7.41 (m, 2 H) 7.41-7.50 (m, 2 H) 7.65-7.74 (m, 2 H) 7.76-7.86 (m, 2 H) MS (ESI), m/z 404.0 (M+H)+.

Provenance & Evidence