Triethyl phosphite → Diethyl[(5-bromo-1,3-thiazol-2-yl)methyl]phosphonate

Participants

Reaction Steps

5-Bromo-2-(bromomethyl)-1,3-thiazole (1.02 g, 3.97 mmol) and triethyl phosphite (1.389 mL, 7.94 mmol) were combined in toluene (8 mL) and stirred at reflux overnight. The reaction was cooled to room temperature and concentrated in vacuo. The residue was purified by chromatography on silica gel (0-5% methanol in ethyl acetate) to afford diethyl[(5-bromo-1,3-thiazol-2-yl)methyl]phosphonate as a yellow oil. MS ESI calc'd. for C8H14BrNO3PS [M+H]+ 314, 316. found 314, 316. 1H NMR (500 MHz, CDCl3) δ 7.59 (s, 1H), 4.17-4.09 (m, 4H), 3.57 (d, J=21.2 Hz, 2H), 1.32 (t, J=7.1 Hz, 6H).

Provenance & Evidence