1-(2-bromophenyl)ethane-1,2-diol

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a stirred solution of 1-(2-bromophenyl)ethane-1,2-diol (step 1, 5.01 g, 22.6 mmol) and in dichloromethane (20 mL) and imidazole (2.31 g, 33.9 mmol) in N,N-dimethylformamide (20 mL) was added tert-butyldiphenylsilyl chloride (6.53 g, 23.8 mmol) at 0° C. and the mixture was stirred for 19 h at the same temperature. The reaction mixture was diluted with toluene/ethyl acetate (1/3), then washed with water for three times and brine, dried over sodium sulfate, and evaporated. The residue was purified by column chromatography on silica gel (100 g) eluting with hexane/ethyl acetate (10/1) to afford 7.05 g (68%) of the title compound as a colorless syrup: washed with water for three times and brine dried over sodium sulfate evaporated The residue was purified by column chromatography on silica gel (100 g) eluting with hexane/ethyl acetate (10/1)

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

Procedure: To a stirred solution of 1-(2-bromophenyl)ethane-1,2-diol (step 1, 5.01 g, 22.6 mmol) and in dichloromethane (20 mL) and imidazole (2.31 g, 33.9 mmol) in N,N-dimethylformamide (20 mL) was added tert-butyldiphenylsilyl chloride (6.53 g, 23.8 mmol) at 0° C. and the mixture was stirred for 19 h at the same temperature. The reaction mixture was diluted with toluene/ethyl acetate (1/3), then washed with water for three times and brine, dried over sodium sulfate, and evaporated. The residue was purified by column chromatography on silica gel (100 g) eluting with hexane/ethyl acetate (10/1) to afford 7.05 g (68%) of the title compound as a colorless syrup: washed with water for three times and brine dried over sodium sulfate evaporated The residue was purified by column chromatography on silica gel (100 g) eluting with hexane/ethyl acetate (10/1)

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

Procedure: To a stirred solution of 1-bromo-2-vinylbenzene (4.14 g, 22.6 mmol) and 4-methylmorpholine N-oxide in acetonitrile (20 mL) and water (10 mL) was added a 2.5% solution of osmium tetroxide in 2-methyl-2-propanol (2 mL) at room temperature and the mixture was stirred for 24 h at the same temperature. The reaction mixture was quenched by the addition of sodium hydrosulfate, and diluted with water, then extracted with ethyl acetate. The organic layer washed with diluted hydrochloric acid aqueous solution and brine, dried over sodium sulfate, and evaporated to afford 5.01 g (quant.) of the title compound as a brown solid: The reaction mixture was quenched by the addition of sodium hydrosulfate diluted with water extracted with ethyl acetate The organic layer washed with diluted hydrochloric acid aqueous solution and brine dried over sodium sulfate evaporated

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a stirred solution of 1-bromo-2-vinylbenzene (4.14 g, 22.6 mmol) and 4-methylmorpholine N-oxide in acetonitrile (20 mL) and water (10 mL) was added a 2.5% solution of osmium tetroxide in 2-methyl-2-propanol (2 mL) at room temperature and the mixture was stirred for 24 h at the same temperature. The reaction mixture was quenched by the addition of sodium hydrosulfate, and diluted with water, then extracted with ethyl acetate. The organic layer was washed with diluted hydrochloric acid aqueous solution and brine, dried over sodium sulfate, and evaporated to afford 5.01 g (quant.) of the title compound as a brown solid: The reaction mixture was quenched by the addition of sodium hydrosulfate diluted with water extracted with ethyl acetate The organic layer was washed with diluted hydrochloric acid aqueous solution and brine dried over sodium sulfate evaporated

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

Procedure: To a stirred solution of 1-(2-bromophenyl)ethane-1,2-diol (step 1, 5.01 g, 22.6 mmol) and in dichloromethane (20 mL) and imidazole (2.31 g, 33.9 mmol) in N,N-dimethylformamide (20 mL) was added tert-butyldiphenylsilyl chloride (6.53 g, 23.8 mmol) at 0° C. and the mixture was stirred for 19 h at the same temperature. The reaction mixture was diluted with toluene/ethyl acetate (1/3), then washed with water for three times and brine, dried over sodium sulfate, and evaporated. The residue was purified by column chromatography on silica gel (100 g) eluting with hexane/ethyl acetate (10/1) to afford 7.05 g (68%) of the title compound as a colorless syrup: washed with water for three times and brine dried over sodium sulfate evaporated The residue was purified by column chromatography on silica gel (100 g) eluting with hexane/ethyl acetate (10/1)

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

Procedure: To a stirred solution of 1-bromo-2-vinylbenzene (4.14 g, 22.6 mmol) and 4-methylmorpholine N-oxide in acetonitrile (20 mL) and water (10 mL) was added a 2.5% solution of osmium tetroxide in 2-methyl-2-propanol (2 mL) at room temperature and the mixture was stirred for 24 h at the same temperature. The reaction mixture was quenched by the addition of sodium hydrosulfate, and diluted with water, then extracted with ethyl acetate. The organic layer washed with diluted hydrochloric acid aqueous solution and brine, dried over sodium sulfate, and evaporated to afford 5.01 g (quant.) of the title compound as a brown solid: The reaction mixture was quenched by the addition of sodium hydrosulfate diluted with water extracted with ethyl acetate The organic layer washed with diluted hydrochloric acid aqueous solution and brine dried over sodium sulfate evaporated