反应详情

To a 250 ml flask fitted with reflux condenser, thermometer, and nitrogen inlet were added 4-nitrobenzil (10.83 g, 42.49 mmol), 3-bromophenol (7.35 g, 42.49 mmol) and dimethylsulfoxide (150 ml). After stirring at room temperature for 20 minutes under a nitrogen atmosphere, potassium carbonate (11.73 g, 84.98 mmol) was added to the flask and the flask was heated to an internal temperature of 95° C. for 19 h under nitrogen. When cooled to room temperature the solution was very slowly poured into 12N HCL(500 ml) and extracted with methylene chloride (2×100 ml). The organic layer was washed with water (3×500 ml), dried over anhydrous magnesium sulfate, and evaporated to dryness by rotary evaporation. The light orange oil was then dissolved in 4:1 hexane:methylene chloride and chromatographed on a silica gel column (Woelm DCC, 211.94 g, 5 cm dia×24 cm H). The purified product was recrystallized twice from methylene chloride:methanol (25 ml:150 ml) to afford light yellow crystals (11.08 g, 69%): mp 75°-76° C.

1. customTo a 250 ml flask fitted
2. temperaturewith reflux condenser
3. temperaturethe flask was heated to an internal temperature of 95° C. for 19 h under nitrogen
4. temperatureWhen cooled to room temperature the solution
5. additionwas very slowly poured into 12N HCL(500 ml)
6. extractionextracted with methylene chloride (2×100 ml)
7. washThe organic layer was washed with water (3×500 ml)
8. dry with materialdried over anhydrous magnesium sulfate
9. customevaporated to dryness by rotary evaporation
10. dissolutionThe light orange oil was then dissolved in 4:1 hexane
11. custommethylene chloride and chromatographed on a silica gel column (Woelm DCC, 211.94 g, 5 cm dia×24 cm H)
12. customThe purified product was recrystallized twice from methylene chloride