Aniline → HCID 54201940, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.0 g (1.18 mmol) of bis(9-fluorenyl)-methyl chloroformate in 15 mL of freshly distilled THF and 15 mL of dry benzene was added 0.21 mL (2.3 mmol) of freshly distilled aniline in one portion at 0° C. The mixture was stirred at 0° C. for 3 hours and quenched with 10 mL of sat'd NH4Cl. The organic layer was washed with water (10mL) and the pooled aqueous layer was extracted with CHCl3 (2×10 mL). The combined organic extracts were dried over MgSO4 and the solvent was evaporated in vacuo to give 1.13 g (100%) of the crude urethane as a white solid. Recrystallization from chloroform gave 0.93 g (82.03%) of the pure α-F-Fmoc-aniline as white crystals, m.p. 225°-227° C. (dec.); IR (KBr): 3340 (NH), 1705 (C=O) cm-1 ; 1H NMR (DMSO-d6): δ 4.59 (d, 2H, ArCH), 5.70 (t, 1H, CHO), 6.80-7.95 (m, 21H, aryl), 9.38 (b, 1H, NH).

Provenance & Evidence