Methyl iodide → 1-Bromo-3-tert-butyl-5-(1,1-dimethoxyethyl)-2-methoxybenzene

Participants

Reaction Steps

To 1-(5-bromo-3-tert-butyl-4-hydroxyphenyl)ethanone (678 g, 2.50 mol), methanol (678 mL), trimethyl orthoformate (796 g, 7.50 mol) and (±)-10-camphorsulfonic acid [(±)-CSA] (11.6 g, 0.050 mol, 2 mol %) were added and stirred under a nitrogen atmosphere. Alter stirring for 2.7 hours, N,N-dimethylformamide (1.7 L) were added thereto. The resultant mixture was cooled on ice. Subsequently, methyl iodide (700 g) and potassium carbonate (518 g) were added in this order and stirred at room temperature. After stirring for 5.5 hours, water (4750 mL) and n-heptane (4750 mL) were added to the reaction solution to separate liquid layers. The organic layer was washed with water (2370 mL), and sodium sulfate (120.2 g) was added thereto and stirred. Then, this layer was vacuum filtered. At this time, washing with n-heptane (250 mL) was carried out. The solvent in the filtrate was evaporated (50° C.) to give 808 g of the captioned compound as a brown oily material (yield: 98%; HPLC purity: 96.8%).

Provenance & Evidence