Hydrochloric Acid → HCID 67275555, compound

Participants

Reaction Steps

To magnesium turnings (888 mg) in diethyl ether (60 mL) was added 1-bromo-4-[(cyclopropylmethyl)thio]benzene (8.4 g). The mixture was heated at reflux for 16 hrs, and then cooled to ambient temperature. A solution of 2-methyl-2-[(trimethylsilyl)oxy]propanenitrile (4.35 g) in diethyl ether (30 mL) was then added and this solution was stirred at ambient temperature for 7 h. Sodium borohydride (1.33 g) in methanol (30 mL) was then slowly added and the solution aged for 2 h Water (25 mL) was added followed by 1N hydrochloric acid (100 mL) and the mixture stirred for 1 h. The organic layer was extracted with a further portion of 1N hydrochloric acid (100 mL) and the acid extracts combined. These were then made basic with 4N sodium hydroxide solution and extracted with dichloromethane (2×100 mL). The organic extracts were dried (MgSO4) and concentrated to give the title compound as a yellow solid (3.7 g). 1H NMR (360 MHz, CDCl3): δ 7.22-7.34 (4H, m), 3.77 (1H, s), 2.85 (2H, d, J=7.0 Hz), 1.21 (3H, s), 1.09-1.03 (1H, m), 1.03 (3H, s), 0.57 (2H, q, J=5.1 Hz), 0.24 (2H, q, J=5.1 Hz); m/z 307 (M-16[NH2])+.

Provenance & Evidence