Hydrogen Bromide → 2,3-Dihydro-5-phenyl-4-benzofuranamine

Participants

Reaction Conditions

Reaction Steps

A pressure bottle was charged with N-[3-(2-hydroxyethyl)-4-methoxy-[1,1'-biphenyl]-2-yl]-2,2-dimethylpropanamide (10.77 g, 32.9 mmol), 48% HBr solution (200 mL), flushed with nitrogen, capped, and stirred at 95° C. for 12 h. The suspension was cooled to room temperature and poured over 200 g of ice/water. The aqueous phase was washed with Et2O (2×100 mL) and concentrated in vacuo to give a tan solid. The solid was redigested with H2O (200 mL), concentrated in vacuo, and dried (0.5 mm, 18 h). The resultant solid was digested with 1 N NaOH (300 mL), the resultant suspension extracted with CH2Cl2 (3×300 mL), and the combined extracts dried (K2CO3), filtered, and concentrated in vacuo to give the free amine (2.01 g, 21%) as an oil. 1H NMR (300 MHz, CDCl3) δ 3.05 (t, J=8.5 Hz, 2H), 4.64 (t, J=8.5 Hz, 2H), 6.34 (d, J=8 Hz, 1H), 6,91 (d, J=8 Hz, 1H), 7.29-7.45 (m, 7H).

Provenance & Evidence