p-Fluoronitrobenzene → Methyl 3,5-bis(4-nitrophenoxy)benzoate

Participants

Reaction Steps

A mixture of potassium carbonate (98.72 g, 0.714 mol) and 550 ml of N,N-dimethylacetamide (DMAC) is added to a 1L, three-necked round-bottom flask equipped with an overhead stirrer, condenser and a nitrogen inlet tube. Nitrogen is bubbled through the solution for 1 hour, following which methyl 3,5-dihydroxybenzoate (60.00 g, 0.357 mol) and 1-fluoro-4-nitrobenzene (100.79 g, 0.714 mol) are added. The slurry solution is stirred and heated to 80°-90° C. under nitrogen for 10 hours, and the mixture is then filtered while hot to remove inorganic salts. The filtrate is kept in a freezer overnight and the yellow crystals are collected by filtration, washed with water and dried. The product is recrystallized from ethyl acetate to yield 68 percent of yellow crystals: mp 180.5°-182.0° C.

Provenance & Evidence