4-Fluorophenol → HCID 70654247, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (11.24 g, 281.00 mmol) in anhydrous N,N-dimethylformamide (500 mL) was added 4-fluorophenol (26.21 g, 233.96 mmol) at 0° C. After hydrogen evolution had ceased, bromo-acetaldehyde diethyl acetal (55 g, 280.60 mmol) was added. The reaction was heated at 120° C. overnight. The mixture was poured into ice-water, extracted with ethyl acetate (3×150 mL), washed with 1N sodium hydroxide (3×100 mL), and brine (3×100 mL). The organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was removed under vacuum to give the residue, which was purified by a silica gel column with 1% ethyl acetate in petroleum ether to afford 1-(diethoxymethoxy)-4-fluorobenzene as oil (45 g, 84%).

Provenance & Evidence