Ammonium Chloride → 4-Bromo-5-(methoxymethoxy)-2-methylpyridine

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Reaction Steps

A solution of 1000 mg (6.53 mmol) 5-methoxymethoxy-2-methyl-pyridine (J.-P. Behr et al. Bioorg. Med. Chem. Lett. 2003, 13(10), 1713) in 10 mL THF was cooled to −78° C., where 4.03 mL (6.85 mmol) t-BuLi (1.7M solution in pentane) was added. The resulting mixture was stirred under argon for 1 h, then 2.126 g (6.53 mmol) 1,2-dibromotetrachloroethane (in 5 mL THF) was added. Stirring was continued for 1 h at −78° C. and the reaction mixture was warmed to rt. Saturated NH4Cl solution was added and the aqueous mixture was extracted with EtOAc (2×). The combined organic layers were washed with H2O and brine, dried (MgSO4) and filtered. The filtrate was concentrated in vacuo to leave a residue that was purified on silica gel (EtOAc/hexane=1:1) to afford 920 mg of the title compound as an oil. LCMS: tR=0.29 min, M+H=232 (79Br), 234 (81Br) (method J).

Provenance & Evidence