2-bromo-5-(2-ethoxyethylsulfanyl)-1,3-dimethylbenzene

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-[(4-Bromo-3,5-dimethylphenyl)thio]ethyl ethyl ether (2.41 g, 8.33 mmol) and (3-formylphenyl)boronic acid (1.37 g, 9.16 mmol) were dissolved in a mixture of 2 M aqueous sodium carbonate solution (24 mL), ethanol (8 mL) and toluene (24 mL), the air was substituted with argon gas, and tetrakis(triphenylphosphine)palladium(0) (0.48 g, 0.42 mmol) was added. The reaction mixture was stirred under an argon atmosphere at 80° C. for 16 hr. After cooling the reaction mixture, saturated brine was added and the mixture was extracted with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=5/1) to give the title compound (1.00 g, yield 38%) as a colorless oil. was added was added the mixture was extracted with diethyl ether The organic layer was dried over anhydrous magnesium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=5/1)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-[(4-Bromo-3,5-dimethylphenyl)thio]ethyl ethyl ether (2.41 g, 8.33 mmol) and (3-formylphenyl)boronic acid (1.37 g, 9.16 mmol) were dissolved in a mixture of 2 M aqueous sodium carbonate solution (24 mL), ethanol (8 mL) and toluene (24 mL), the air was substituted with argon gas, and tetrakis(triphenylphosphine)palladium(0) (0.48 g, 0.42 mmol) was added. The reaction mixture was stirred under an argon atmosphere at 80° C. for 16 hr. After cooling the reaction mixture, saturated brine was added and the mixture was extracted with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=5/1) to give the title compound (1.00 g, yield 38%) as a colorless oil. was added was added the mixture was extracted with diethyl ether The organic layer was dried over anhydrous magnesium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=5/1)

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

Procedure: To a solution of 2-[(3,5-dimethylphenyl)thio]ethyl ethyl ether (2.69 g, 12.8 mmol) in acetic acid (60 mL) was slowly added dropwise a solution of bromine (0.68 mL, 13.2 mmol) in acetic acid (30 mL) under stirring at room temperature. The reaction mixture was stirred at the same temperature for 2 hr, poured into cold water, and the mixture was extracted with diethyl ether. The extract was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=20/1) to give the title compound (2.41 g, yield 65%) as a pale-yellow oil. The reaction mixture was stirred at the same temperature for 2 hr the mixture was extracted with diethyl ether The extract was washed with water and saturated brine dried over anhydrous sodium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=20/1)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-[(4-Bromo-3,5-dimethylphenyl)thio]ethyl ethyl ether (2.41 g, 8.33 mmol) and (3-formylphenyl)boronic acid (1.37 g, 9.16 mmol) were dissolved in a mixture of 2 M aqueous sodium carbonate solution (24 mL), ethanol (8 mL) and toluene (24 mL), the air was substituted with argon gas, and tetrakis(triphenylphosphine)palladium(0) (0.48 g, 0.42 mmol) was added. The reaction mixture was stirred under an argon atmosphere at 80° C. for 16 hr. After cooling the reaction mixture, saturated brine was added and the mixture was extracted with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=5/1) to give the title compound (1.00 g, yield 38%) as a colorless oil. was added was added the mixture was extracted with diethyl ether The organic layer was dried over anhydrous magnesium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=5/1)

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

Procedure: To a solution of 2-[(3,5-dimethylphenyl)thio]ethyl ethyl ether (2.69 g, 12.8 mmol) in acetic acid (60 mL) was slowly added dropwise a solution of bromine (0.68 mL, 13.2 mmol) in acetic acid (30 mL) under stirring at room temperature. The reaction mixture was stirred at the same temperature for 2 hr, poured into cold water, and the mixture was extracted with diethyl ether. The extract was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=20/1) to give the title compound (2.41 g, yield 65%) as a pale-yellow oil. The reaction mixture was stirred at the same temperature for 2 hr the mixture was extracted with diethyl ether The extract was washed with water and saturated brine dried over anhydrous sodium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=20/1)