Boron tribromide → HCID 57991589, compound

Participants

Reaction Steps

To 50 ml eggplant-shaped bottle were added 0.60 g (1.64 mmol) 4-[5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-morpholine prepared in Example 70 and 20 ml dichloromethane. The resulting mixture was cooled in ice-bath, added dropwise 2.4 ml (4.92 mmol) 2.034 mol/L solution of boron tribromide in dichloromethane, stirred in ice-bath for 1 hour and then at room temperature for 3 hours, added 2 g ice to decompose the complex. The resulting mixture was concentrated under a reduced pressure to remove dichloromethane, dissolved in 100 ml ethyl acetate, and washed with saturated brine, dried over anhydrous sodium sulfate, concentrated, purified under a reduced pressure by silica gel column chromatography eluted with dichloromethane and methanol at a ratio 10:1-5:1 (V:V) to give a 0.26 g pale yellow thick liquid in a yield of 44.8%, 1H-NMR (DMSO-d6, 400 MHz) δ: 3.50 (2H, m, CH2), 3.63 (2H, m, CH2), 3.97 (2H, s, CH2), 4.27 (4H, s, CH2), 5.18 (1H, m), 6.97 (2H, d, J=8.40 Hz, ArH), 7.15˜7.40 (7H, m, ArH), 10.14 (1H, s, OH); EI-MS m/e (%): 352.0 (M+, 37), 322.0 (100), 240.0 (48); HREI-MS Calcd. for C20H20N2O2S: 352.1245. found: 352.1243.

Provenance & Evidence