p-Fluoronitrobenzene → 1-[2,4-Bis(methoxymethoxy)-6-(4-nitrophenoxy)phenyl]ethanone

Participants

Reaction Steps

To a stirred suspension of 1-[2-hydroxy-4,6-bis(methoxymethoxy)phenyl]ethanone (78 g, 298 mmol) and K2CO3 (45.3 g, 328 mmol) in DMSO (500 mL) and water (40 ml) was added 4-nitro-1-fluorobenzene (46.3 g, 328 mmol, 1.1 eq). After stirring for 15 min. at room temperature, the resulting suspension was heated for 6 hours at 55° C. After cooling, the dark solution was diluted with ethyl acetate (2000 mL) and thoroughly washed with 10% citric acid solution, then with brine and dried over Na2SO4. The solvent was removed and the residue was columned over silica gel eluting with cyclohexane/ethyl acetate 3/1, to provide the title compound (56 g, 52% yield).

Provenance & Evidence