1-chloro-4-(2,2-diethoxyethoxy)benzene

反応条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1-chloro-4-(2,2-diethoxyethoxy)benzene (45 g, 184 mmol,) in benzene (200 mL) was added polyphosphoric acid (25 g, 221 mmol) with stirring for 2.5 h at 90° C. in an oil bath. The reaction mixture was cooled to room temperature and decanted from the polyphosphoric acid. The solvent was removed under vacuum. The residue was applied onto a silica gel column with 1% ethyl acetate in petroleum ether to afford 5-chlorobenzofuran as colorless oil (14.0 g, crude). The reaction mixture was cooled to room temperature decanted from the polyphosphoric acid The solvent was removed under vacuum

反応条件: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a suspension of sodium hydride (11.24 g, 281 mmol) in anhydrous N,N-dimethylformamide (500 mL) was added 4-chlorophenol (30 g, 234 mmol) at 0° C. After hydrogen evolution had ceased, bromo-acetaldehyde diethyl acetal (55 g, 281 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. The residue was purified by a silica gel column with 1% ethyl acetate in petroleum ether to afford 1-chloro-4-(2,2-diethoxyethoxy)benzene as oil (45 g, 75%). 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 filtered The solvent was removed under vacuum The residue was purified by a silica gel column with 1% ethyl acetate in petroleum ether