Pyridine → HCID 67693831, compound

Participants

Reaction Steps

A stirred solution of phosphorous tribromide (0.31 g, 1.16 mmol) and pyridine (0.057 g, 0.72 mmol) in petroleum ether (18 mL) was cooled to -10° C. under argon. The mixture was treated with a solution of 35 (0.94 g, 3.62 mmol) in anhydrous diethyl ether (18 mL). The reaction mixture was allowed to warm to room temperature over 2.5 h. The solution was then diluted with diethyl ether and washed twice with water. The aqueous layers were combined and back-extracted with another portion of diethyl ether. The organic layers were combined, washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated to give 1.00 g (86%) of 36 as an off-white solid. The bromide was used without purification in the next reaction. 1H NMR (300 MHz, CDCl3) δ7.33 (d, 1H, ArH), 7.28 (d, 1H, ArH), 7.18 (dd, J=12 Hz, 1H, ArH), 6.05 (t, J=9 Hz, 1H, C=CH), 4.12 (d, J=9 Hz, 2H, CH2Br), 2.13 (s, 3H, CH=CCH3), 1.68 (s, 4H, CH2CH2), 1.26 (s, 6H, 2'CH3), and 1.24 (s, 6H, 2×CH3).

Provenance & Evidence