2-iodo-1-phenylethanone

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

Procedure: A mixture of 2-iodoacetophenone (1 g, 4.1 mmol) and hydroxy(tosyloxy)iodobenzene (1.86 g, 4.92 mmol) in dimethylsulfoxide:water (40 mL:2 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 40% ethyl acetate/isohexane, to give 2-hydroxy-1-(2-iodophenyl)ethanone (126 mg, 12%). δH (400 MHz, d6 DMSO): 7.94 (1H, dd, J=0.9, 7.8 Hz), 7.54 (1H, dd, J=1.8, 7.7 Hz), 7.49-7.45 (1H, m), 7.25-7.21 (1H, m), 5.37 (1H, t, J=6.0 Hz), 4.52 (2H, d, J=6.0 Hz). The reaction mixture was partitioned between water and ethyl acetate The organic layer was washed with brine dried over MgSO4 concentrated in vacuo The residue was purified by flash column chromatography on silica eluting with 40% ethyl acetate/isohexane

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

Procedure: A mixture of 2-iodoacetophenone (1 g, 4.1 mmol) and hydroxy(tosyloxy)iodobenzene (1.86 g, 4.92 mmol) in dimethylsulfoxide:water (40 mL:2 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 40% ethyl acetate/isohexane, to give 2-hydroxy-1-(2-iodophenyl)ethanone (126 mg, 12%). δH (400 MHz, d6 DMSO): 7.94 (1H, dd, J=0.9, 7.8 Hz), 7.54 (1H, dd, J=1.8, 7.7 Hz), 7.49-7.45 (1H, m), 7.25-7.21 (1H, m), 5.37 (1H, t, J=6.0 Hz), 4.52 (2H, d, J=6.0 Hz). The reaction mixture was partitioned between water and ethyl acetate The organic layer was washed with brine dried over MgSO4 concentrated in vacuo The residue was purified by flash column chromatography on silica eluting with 40% ethyl acetate/isohexane

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

Procedure: A mixture of 2-iodoacetophenone (1 g, 4.1 mmol) and hydroxy(tosyloxy)iodobenzene (1.86 g, 4.92 mmol) in dimethylsulfoxide:water (40 mL:2 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 40% ethyl acetate/isohexane, to give 2-hydroxy-1-(2-iodophenyl)ethanone (126 mg, 12%). δH (400 MHz, d6 DMSO): 7.94 (1H, dd, J=0.9, 7.8 Hz), 7.54 (1H, dd, J=1.8, 7.7 Hz), 7.49–7.45 (1H, m), 7.25–7.21 (1H, m), 5.37 (1H, t, J=6.0 Hz), 4.52 (2H, d, J=6.0 Hz). The reaction mixture was partitioned between water and ethyl acetate The organic layer was washed with brine dried over MgSO4 concentrated in vacuo The residue was purified by flash column chromatography on silica eluting with 40% ethyl acetate/isohexane

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

Procedure: 2-Iodoacetophenone (6.30 g) was dissolved in methanol (50 ml), sodium borohydride (726 mg) was added and the mixture was stirred at room temperature for 1.5 hr. 10% Aqueous citric acid was added to the reaction mixture and ethanol was evaporated. Water was added and the mixture was extracted 3 times with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and brine, and dried over sodium sulfate. The organic layer was concentrated under reduced pressure and the obtained residue was dissolved in tetrahydrofuran (50 ml). The solution was cooled to 0° C., sodium hydride (1.54 g, 60% in oil), (R)-glycidyl nosylate (9.95 g) and dimethyl sulfoxide (10 ml) were successively added, and the mixture was stirred overnight at 0° C.—room temperature. 10% Aqueous citric acid was added to neutralize the reaction mixture, and extracted 3 times with ethyl acetate. The organic layer was washed successively with water (twice) and brine, and dried over sodium sulfate. The organic layer was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give the title compound (6.36 g). was evaporated Water was added the mixture was extracted 3 times with ethyl acetate The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and brine dried over sodium sulfate The organic layer was concentrated under reduced pressure the obtained residue was dissolved in tetrahydrofuran (50 ml) The solution was cooled to 0° C. sodium hydride (1.54 g, 60% in oil), (R)-glycidyl nosylate (9.95 g) and dimethyl sulfoxide (10 ml) were successively added the mixture was stirred overnight at 0° C.—room temperature 10% Aqueous citric acid was added extracted 3 times with ethyl acetate The organic layer was washed successively with water (twice) and brine dried over sodium sulfate The organic layer was concentrated under reduced pressure the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)