1,2-dibromo-3-chloropropane

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

Procedure: One equivalent of 5-(3-chlorophenyl)-3-(2-(3,4-dihydroxyphenyl)-1-methylethyl)-2-oxazolidinone, prepared by the procedure of U.S. Pat. No. 5,061,727, Example 1, is combined with two equivalents of 2N sodium methoxide in methyl alcohol and the resulting slurry is stirred at room temperature for 30 minutes. One equivalent of 1,2-dibromo-3-chloropropane is added and the stirring is continued at room temperature for 24 hours. The solvent is evaporated in vacuo and the residue is dissolved in methylene chloride. The organic layer is dried, filtered through a pad of hydrous magnesium silicate and the filtrate is evaporated in vacuo to give 2-and 3- chloromethyl-6-(2-(5-(3-chloro-phenyl)-2-oxo-3-oxazolidinyl)propyl)-1,4-benzodioxane. The individual, 2- and 3- isomers, are separated by chromatography. the stirring is continued at room temperature for 24 hours The solvent is evaporated in vacuo the residue is dissolved in methylene chloride The organic layer is dried filtered through a pad of hydrous magnesium silicate the filtrate is evaporated in vacuo

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

Procedure: To a mixed solution of 0.55 g (0.005 mole) of 1-cyanomethylimidazole, 0.4 g (0.005 mole) of carbon disulfide and 10 ml of dimethyl sulfoxide was added 0.8 g (0.014 mole) of potassium hydroxide power with stirring, and the reaction was carried out at room temperature for 1 hour. Then, 1.4 g (0.006 mole) of 1,2-dibromo-3-chloropropane was added dropwise with stirring, and the resulting solution was subjected to reaction for 2 hours. After completion of the reaction, 20 ml of water was added to the reaction solution, after which the resulting mixture was subjected to extraction with ethyl acetate, and the organic layer was washed with water and dried. The solvent was distilled off and the residue was purified by silica gel chromatography and recrystallized from ethyl acetate-n-hexane to obtain 0.8 g of the desired compound in the form of colorless crystals: melting point 96.2° C., yield 62%. with stirring the resulting solution was subjected to reaction for 2 hours was added to the reaction solution after which the resulting mixture was subjected to extraction with ethyl acetate the organic layer was washed with water dried The solvent was distilled off the residue was purified by silica gel chromatography recrystallized from ethyl acetate-n-hexane

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

Procedure: One equivalent of 5-(3-chlorophenyl)-3-(2-(3,4-dihydroxyphenyl)-1-methylethyl)-2-oxazolidinone, prepared by the procedure of U.S. Pat. No. 5,061,727, Example 1, is combined with two equivalents of 2N sodium methoxide in methyl alcohol and the resulting slurry is stirred at room temperature for 30 minutes. One equivalent of 1,2-dibromo-3-chloropropane is added and the stirring is continued at room temperature for 24 hours. The solvent is evaporated in vacuo and the residue is dissolved in methylene chloride. The organic layer is dried, filtered through a pad of hydrous magnesium silicate and the filtrate is evaporated in vacuo to give 2-and 3- chloromethyl-6-(2-(5-(3-chloro-phenyl)-2-oxo-3-oxazolidinyl)propyl)-1,4-benzodioxane. The individual, 2- and 3- isomers, are separated by chromatography. the stirring is continued at room temperature for 24 hours The solvent is evaporated in vacuo the residue is dissolved in methylene chloride The organic layer is dried filtered through a pad of hydrous magnesium silicate the filtrate is evaporated in vacuo

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

Procedure: To a mixed solution of 0.55 g (0.005 mole) of 1-cyanomethylimidazole, 0.4 g (0.005 mole) of carbon disulfide and 10 ml of dimethyl sulfoxide was added 0.8 g (0.014 mole) of potassium hydroxide power with stirring, and the reaction was carried out at room temperature for 1 hour. Then, 1.4 g (0.006 mole) of 1,2-dibromo-3-chloropropane was added dropwise with stirring, and the resulting solution was subjected to reaction for 2 hours. After completion of the reaction, 20 ml of water was added to the reaction solution, after which the resulting mixture was subjected to extraction with ethyl acetate, and the organic layer was washed with water and dried. The solvent was distilled off and the residue was purified by silica gel chromatography and recrystallized from ethyl acetate-n-hexane to obtain 0.8 g of the desired compound in the form of colorless crystals: melting point 96.2° C., yield 62%. with stirring the resulting solution was subjected to reaction for 2 hours was added to the reaction solution after which the resulting mixture was subjected to extraction with ethyl acetate the organic layer was washed with water dried The solvent was distilled off the residue was purified by silica gel chromatography recrystallized from ethyl acetate-n-hexane

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

Procedure: One equivalent of 5-(3-chlorophenyl)-3-(2-(3,4-dihydroxyphenyl)-1-methylethyl)-2-oxazolidinone, prepared by the procedure of U.S. Pat. No. 5,061,727, Example 1, is combined with two equivalents of 2N sodium methoxide in methyl alcohol and the resulting slurry is stirred at room temperature for 30 minutes. One equivalent of 1,2-dibromo-3-chloropropane is added and the stirring is continued at room temperature for 24 hours. The solvent is evaporated in vacuo and the residue is dissolved in methylene chloride. The organic layer is dried, filtered through a pad of hydrous magnesium silicate and the filtrate is evaporated in vacuo to give 2-and 3- chloromethyl-6-(2-(5-(3-chloro-phenyl)-2-oxo-3-oxazolidinyl)propyl)-1,4-benzodioxane. The individual, 2- and 3- isomers, are separated by chromatography. the stirring is continued at room temperature for 24 hours The solvent is evaporated in vacuo the residue is dissolved in methylene chloride The organic layer is dried filtered through a pad of hydrous magnesium silicate the filtrate is evaporated in vacuo