3-Bromophenol → HCID 14097602, compound

Participants

Reaction Steps

To 60% sodium hydride (9.8 g, 245 mmol) in 250 mL dimethylformamide at 5° C. under nitrogen is added portionwise 3-bromophenol (42.6 g, 246 mmol). After thirty minutes a solution of 2-(chloromethyl)quinoline (43.6 g, 246 mmol) in 250 mL dimethylformamide is rapidly added. The reaction is allowed to warm to room temperature. After overnight stirring, the reaction is freed of solvent and then partitioned between 1N sodium hydroxide and methylene chloride. The organic layer is separated, dried over magnesium sulfate and evaporated to 67.9 g of a yellow solid. Recrystallization from acetonitrile affords 42.8 g (55%) of brown crystals, m.p. 79°-81° C.

Provenance & Evidence