4-bromo-3,5-dimethylbenzenethiol

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

Procedure: Dimethyl-thiocarbamic acid S-(4-bromo-3,5-dimethyl-phenyl)ester (5.78 g, 20.14 mmol) was diluted with methanol (50 mL) and to this was added sodium methoxide (4.75 mL of 4.25M in methanol, 20.14 mmol). The reaction was heated to reflux under nitrogen and monitored by TLC. After complete conversion, 20 h., the reaction was allowed to cool to room temperature. The reaction was neutralized with 1N HCl (7.5 mL) and diluted with ethyl acetate (150 mL). The two phases were separated and the organic layer was washed with water (75 mL), then brine (75 mL). The organic layer was then dried over anhydrous sodium sulfate, then concentrated and loaded onto silica gel column. The title compound was purified using flash column chromatography, yielding 4.0 g, or 92%. The reaction was heated to reflux under nitrogen After complete conversion, 20 h. The two phases were separated the organic layer was washed with water (75 mL) The organic layer was then dried over anhydrous sodium sulfate concentrated The title compound was purified yielding 4.0 g, or 92%

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

Procedure: Dimethyl-thiocarbamic acid S-(4-bromo-3,5-dimethyl-phenyl) ester (5.78 g, 20.14 mmol) is diluted with methanol (50 mL) and sodium methoxide (4.75 mL of 4.25M in methanol, 20.14 mmol) is added. The reaction is heated to reflux under nitrogen and monitored by TLC. After complete conversion, 20 hours, the reaction is allowed to cool to room temperature. The reaction is neutralized with 1N hydrochloric acid (7.5 mL) and diluted with ethyl acetate (150 mL). The two phases are separated and the organic layer is washed with water (75 mL), then brine (75 mL). The organic layer is dried over anhydrous sodium sulfate, concentrated and loaded onto silica gel column. The title compound is purified using flash column chromatography, yielding 4.0 g, or 92%. is added The reaction is heated to reflux under nitrogen After complete conversion, 20 hours The two phases are separated the organic layer is washed with water (75 mL) The organic layer is dried over anhydrous sodium sulfate concentrated The title compound is purified yielding 4.0 g, or 92%

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

Procedure: Dimethyl-thiocarbamic acid S-(4-bromo-3,5-dimethyl-phenyl) ester (5.78 g, 20.14 mmol) is diluted with methanol (50 mL) and sodium methoxide (4.75 mL of 4.25M in methanol, 20.14 mmol) is added. The reaction is heated to reflux under nitrogen and monitored by TLC. After complete conversion, 20 hours, the reaction is allowed to cool to room temperature. The reaction is neutralized with 1N hydrochloric acid (7.5 mL) and diluted with ethyl acetate (150 mL). The two phases are separated and the organic layer is washed with water (75 mL), then brine (75 mL). The organic layer is dried over anhydrous sodium sulfate, concentrated and loaded onto silica gel column. The title compound is purified using flash column chromatography, yielding 4.0 g, or 92%. is added The reaction is heated to reflux under nitrogen After complete conversion, 20 hours The two phases are separated the organic layer is washed with water (75 mL) The organic layer is dried over anhydrous sodium sulfate concentrated The title compound is purified yielding 4.0 g, or 92%

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

Procedure: Dimethyl-thiocarbamic acid S-(4-bromo-3,5-dimethyl-phenyl)ester (5.78 g, 20.14 mmol) was diluted with methanol (50 mL) and to this was added sodium methoxide (4.75 mL of 4.25M in methanol, 20.14 mmol). The reaction was heated to reflux under nitrogen and monitored by TLC. After complete conversion, 20 h., the reaction was allowed to cool to room temperature. The reaction was neutralized with 1N HCl (7.5 mL) and diluted with ethyl acetate (150 mL). The two phases were separated and the organic layer was washed with water (75 mL), then brine (75 mL). The organic layer was then dried over anhydrous sodium sulfate, then concentrated and loaded onto silica gel column. The title compound was purified using flash column chromatography, yielding 4.0 g, or 92%. The reaction was heated to reflux under nitrogen After complete conversion, 20 h. The two phases were separated the organic layer was washed with water (75 mL) The organic layer was then dried over anhydrous sodium sulfate concentrated The title compound was purified yielding 4.0 g, or 92%