Phosgene → HCID 11037855, compound

Participants

Reaction Steps

To a solution of 17-(trimethylsilyl)oxymethyl-tetrabenzo(a,c,g,i)fluorene (0.177 g, 0.38 mmol) in dichloromethane (5 ml) was added phosgene (1.5 ml, 2.9 mmol; 7.5 equiv; 1.93M in toluene). The reaction mixture was heated under reflux for 2 h and then stirred at room temperature for 48 h, under nitrogen. The solvent was removed in vacuo to give compound (37) as a yellow solid which was recrystallized from dichloromethane/n-hexane (36.9 mg, 21%); m.p. 188-189° C.; (Found: C, 80.9; H, 4.29; N, 0.45; C31H19O2Cl requires: C, 81.1; H, 4.14%); νmax (CH2Cl2) 3060 (CH stretching, aromatic), 1775 (CO, chloroformate), 1610, 1500 (aromatic rings), 1160, 1140 (CO stretching) cm−1; δH (CDCl3, 200 MHz) 8.79-8.60 (6H, m, aromatic), 8.20-8.15 (2H, m, aromatic), 7.76-7.57 (8H, m, aromatic), 5.17 (1H, t, 3J=5.7 Hz, CH), 4.77 (2H, d, 3J=5.7 Hz, CH2); δc (CDCl3, 50 MHz) 150.5 (CO, chloroformate), 140.3, 137.2, 131.6, 130.5, 128.2, 127.7 (quaternary aromatic C's), 127.5, 127.0, 126.3, 126.2, 125.1, 124.5, 123.5, 123.4 (aromatic CH's), 74.6 (CH2), 46.5 (CH).

Provenance & Evidence