3'-Bromoacetophenone → HCID 68153413, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5-bromo-2-methoxy-pyridine (10.0 g, 1 eq) in dry tetrahydrofuran (50 ml) was treated dropwise at −78° C. under a nitrogen atmosphere with n-butyllithium (1.6N in hexane, 30 ml, 0.9 eq). The mixture was stirred at −78° C. for 1 hour, then was added a solution of 3-bromo acetophenone (7.7 ml, 1.1 eq) in dry tetrahydrofuran (20 mL) at −78° C. The mixture was then allowed to warm to room temperature. The progress of the reaction was checked by TLC (cyclohexane/AcOEt 9:1). After 1 hour conversion to the desired product was complete. For the workup, saturated solution of ammonium chloride (30 ml) was added, the tetrahydrofuran layer was separated, and then the aqueous phase was extracted with dichloromethane (3×20 ml). The organic fractions were collected, dried over sodium sulphate and evaporated. The crude was dissolved in acetic acid (100 ml) and concentrated sulphuric acid (20 ml) was added, and mixture was stirred at room temperature for 2 hours. A solution of sodium hydroxide (15%) was added to the mixture until pH 6-5, then it was extracted with dichloromethane (3×25 ml). The organic phases were collected, dried and evaporated. The crude was purified by flash chromatography eluting with cyclohexane. 10.3 g of The 5-[1-(3-bromo-phenyl)-vinyl]-2-methoxy-pyridine was obtained as colorless oil (10.3 g, 71% of theory). MS (ISP): m/z=291.9 [M+H]+.

Provenance & Evidence