1-(3-bromo-4-hydroxyphenyl)propan-2-one

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Potassium carbonate (2.7 g) and benzyl bromide (2.3 ml) were added to a solution of 1-(3-bromo-4-hydroxyphenyl) acetone (4.0 g) in DMF (40 ml) and the mixture was stirred at room temperature for six hours. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate-n-hexane) to obtain 1-[4-(benzyloxy)-3-bromophenyl]acetone (3.65 g). the mixture was extracted with ethyl acetate The organic layer was washed with water and saturated brine dried over anhydrous sodium sulfate After filtration the solvent was evaporated under reduced pressure The resulting residue was purified by silica gel column chromatography (ethyl acetate-n-hexane)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium acetate (50.5 g) was added to a solution of 3-bromo-4-hydroxyphenylacetic acid (28.5 g) in acetic anhydride (100 ml) and the mixture was refluxed with heating for 21 hours. After cooling to room temperature, 20% aqueous solution of sodium hydroxide was added to the reaction mixture to adjust to pH 11. The mixture was refluxed with heating for one hour. After cooling to room temperature, 10% aqueous solution of hydrochloric acid was added to the reaction mixture to adjust to pH 6. The mixture was extracted with ethyl acetate. The organic layer was washed with water, saturated aqueous solution of sodium bicarbonate, and saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-n-hexane) to obtain 1-(3-bromo-4-hydroxyphenyl) acetone (22.2 g). the mixture was refluxed with heating for 21 hours The mixture was refluxed with heating for one hour After cooling to room temperature The mixture was extracted with ethyl acetate The organic layer was washed with water, saturated aqueous solution of sodium bicarbonate, and saturated brine dried over anhydrous sodium sulfate After filtration the solvent was evaporated under reduced pressure The residue was purified by silica gel column chromatography (ethyl acetate-n-hexane)