Potassium Carbonate → 3-((4-Bromo-3,5-dimethylphenoxy)methyl)-3-methyloxetane

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Reaction Steps

To a solution of 4-bromo-3,5-dimethylphenol (3.0 g) and K2CO3 (5.5 g) in N,N-dimethylformamide (10 mL) is added 3-(bromomethyl)-3-methyloxetane (2.95 g). The mixture is stirred for 12 hours at room temperature and then partitioned between saturated aqueous NaHCO3 solution and ethyl acetate. The aqueous phase is extracted with ethyl acetate and the combined organic phases are dried (MgSO4). The solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 100:0→70:30) to give the title compound. Yield: 3.5 g; LC (method 4): tR=1.81 min; Mass spectrum (ESI+): m/z=285 [M+H]+.

Provenance & Evidence