Methyl iodide → 2-(5-Methoxy-2-methylphenyl)-[1,3]dioxolane

Participants

Reaction Steps

A solution of 2-(2-bromo-5-methoxyphenyl)-1,3-dioxolane (5.44 g; 21 mmol; from step (i) above) in THF (dry, 60 mL) was cooled to −78° C. under a nitrogen atmosphere, and n-BuLi (1.4M; 19.5 mL) was added dropwise via syringe. After addition the solution was stirred at −78° C. for 35 minutes, whereafter MeI (13.41 g; 94.5 mmol) was added. The resultant mixture was slowly stirred to attain room temperature, and then quenched with NH4Cl/aq and extracted with ether. The organic phase was dried (Na2SO4) and concentrated, yielding 4.25 g (quantitative) of the sub-title compound as a brown oil.

Provenance & Evidence