Water → {4-[(2-fluorophenyl)methoxy]phenyl}methanamine

Participants

Reaction Steps

To a LiAlH4 (6.50 g, 171.9 mmol) suspension in THF (500 mL) was added dropwise a THF (40 mL) solution of 4-(2-fluorobenzyloxy)benzonitrile (13.00 g, 57.3 mmol) at 0° C. The mixture was stirred at room temperature (16 h) and H2O (5.4 mL) was added dropwise at 0° C. followed by an aqueous NaOH solution (2.7 mL, 15% w/w), and then H2O (5.4 mL). The mixture was stirred at room temperature (2 h), and the precipitate filtered and washed with CH2Cl2. The filtrate was concentrated in vacuo to obtain a colorless oil (8.00 g, 64%): Rf=0.00 (hexanes/EtOAc 911); IR (hydrochloride salt, nujol) 3081, 1608, 1519, 1457, 1380, 1300, 1240, 1181, 1051, 967, 836, 754, 558 cm−1; 1H NMR (CDCl3) δ 1.63 (br 5, NH2), 3.80 (s, CH2NH2), 5.12 (s, CH2O), 6.96 (d, J=9.0 Hz, 2 ArH), 7.05-7.34 (m, 5 ArH), 7.50 (td, J=1.5, 7.5 Hz, 1 ArH).

Provenance & Evidence