Carbon tetrabromide → 2-(Bromomethyl)-5-chloropyridine

Participants

Reaction Steps

To a 0° C. solution of (5-chloropyridin-2-yl)methanol Part D (10 mg, 0.070 mmol) and triphenylphosphine (32.9 mg, 0.125 mmol) in DCM (0.170 mL) was added a solution of carbon tetrabromide (31.4 mg, 0.095 mmol) in DCM (0.084 mL) dropwise. The mixture was stirred at RT for 2.0 h at which point the solvent was removed in vacuo and the crude product was subjected to flash chromatography (silica gel/DCM-EtOAc 100:0 to 0:100 gradient) to afford 2-(bromomethyl)-5-chloropyridine 16E (2.4 mg, 16.8% yield) as a light brown oil. LC-MS, [M+H]+208. 1H NMR (400 MHz, CDCl3) δ 8.47 (1H, d, J=2.2 Hz), 7.61 (1H, dd, J=8.4, 2.2 Hz), 7.33 (1H, d, J=8.4 Hz), 4.46 (2H, s). HPLC-Method 8; 2.42 min.

Provenance & Evidence