Reaction Steps
To a stirred solution of 4 (715 mg, 1.53 mmol), N-(4-bromobutyl)-phthalimide (888 mg, 3.15 mmol) in 20 mL CH3CN, CsF (1.24 g, 8.21 mmol) was added. The resulting mixture was refluxed for 5 hours and then concentrated in vacuo. MPLC purification (Hex:EtOAc/4:1) of the residue gave 5 as a yellow amorphous solid (666 mg, 74%). 1H NMR (400 MHz, CDCl3) δ 7.96 (s, 1H), 7.78-7.65 (m, 6H), 7.58 (s, 1H), 7.48-7.39 (m, 5H), 6.57 (s, 1H), 4.30 (t, J=7.2 Hz, 2H), 4.16 (q, J=7.2 Hz, 2H), 3.67 (s, 2H), 3.49 (t, J=6.8 Hz, 2H), 1.74-1.68 (m, 2H), 1.50-1.46 (m, 2H), and 1.26 (t, J=7.2 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 187.33, 169.95, 168.50, 145.22, 144.25, 136.85, 135.71, 135.07, 134.18, 132.55, 132.15, 132.09, 130.69, 129.52, 128.96, 128.84, 128.74, 123.44, 121.48, 121.42, 120.53, 112.50, 103.12, 61.49, 43.67, 37.26, 35.37, 27.38, 25.81, and 14.44.
