5-bromo-1,3-dimethyl-2-methylsulfanylbenzene

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

Procedure: Dissolve 5-bromo-1,3-dimethyl-2-methylsulfanyl-benzene (555 mg, 2.42 mmol) in methanol (30 mL) and treat with oxone (6.0 g, 9.8 mmol). Stir the mixture at ambient temperature for 1 hour. Filter the suspension through silica gel and elute with CH2Cl2 (100 mL). Evaporate the filtrate to give 316 mg (50%) of the title compound. Filter the suspension through silica gel elute with CH2Cl2 (100 mL) Evaporate the filtrate

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add 5-bromo-2-fluoro-1,3-dimethyl-benzene (3.5 g, 17.2 mmol) to dimethylformamide (DMF, 30 mL) at ambient temperature followed by sodium thiomethoxide (1.32 g, 17.9 mmol). Heat at 50° C. for 8 hours and dilute with water (10 mL) and diethyl ether (100 mL). Separate the layers, wash the organics with brine, and dry with magnesium sulfate before concentrating to a residue. Chromatograph the residue on a SiO2 column eluting with diethyl ether (20%) in hexane to give 566 mg (14%) of 5-bromo-1,3-dimethyl-2-methylsulfanyl-benzene. Separate the layers wash the organics with brine dry with magnesium sulfate before concentrating to a residue Chromatograph the residue on a SiO2 column eluting with diethyl ether (20%) in hexane

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

Procedure: Dissolve 5-bromo-1,3-dimethyl-2-methylsulfanyl-benzene (555 mg, 2.42 mmol) in methanol (30 mL) and treat with oxone (6.0 g, 9.8 mmol). Stir the mixture at ambient temperature for 1 hour. Filter the suspension through silica gel and elute with CH2Cl2 (100 mL). Evaporate the filtrate to give 316 mg (50%) of the title compound. Filter the suspension through silica gel elute with CH2Cl2 (100 mL) Evaporate the filtrate

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add 5-bromo-2-fluoro-1,3-dimethyl-benzene (3.5 g, 17.2 mmol) to dimethylformamide (DMF, 30 mL) at ambient temperature followed by sodium thiomethoxide (1.32 g, 17.9 mmol). Heat at 50° C. for 8 hours and dilute with water (10 mL) and diethyl ether (100 mL). Separate the layers, wash the organics with brine, and dry with magnesium sulfate before concentrating to a residue. Chromatograph the residue on a SiO2 column eluting with diethyl ether (20%) in hexane to give 566 mg (14%) of 5-bromo-1,3-dimethyl-2-methylsulfanyl-benzene. Separate the layers wash the organics with brine dry with magnesium sulfate before concentrating to a residue Chromatograph the residue on a SiO2 column eluting with diethyl ether (20%) in hexane

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add 5-bromo-2-fluoro-1,3-dimethyl-benzene (3.5 g, 17.2 mmol) to dimethylformamide (DMF, 30 mL) at ambient temperature followed by sodium thiomethoxide (1.32 g, 17.9 mmol). Heat at 50° C. for 8 hours and dilute with water (10 mL) and diethyl ether (100 mL). Separate the layers, wash the organics with brine, and dry with magnesium sulfate before concentrating to a residue. Chromatograph the residue on a SiO2 column eluting with diethyl ether (20%) in hexane to give 566 mg (14%) of 5-bromo-1,3-dimethyl-2-methylsulfanyl-benzene. Separate the layers wash the organics with brine dry with magnesium sulfate before concentrating to a residue Chromatograph the residue on a SiO2 column eluting with diethyl ether (20%) in hexane

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

Procedure: Dissolve 5-bromo-1,3-dimethyl-2-methylsulfanyl-benzene (555 mg, 2.42 mmol) in methanol (30 mL) and treat with oxone (6.0 g, 9.8 mmol). Stir the mixture at ambient temperature for 1 hour. Filter the suspension through silica gel and elute with CH2Cl2 (100 mL). Evaporate the filtrate to give 316 mg (50%) of the title compound. Filter the suspension through silica gel elute with CH2Cl2 (100 mL) Evaporate the filtrate

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add 5-bromo-2-fluoro-1,3-dimethyl-benzene (3.5 g, 17.2 mmol) to dimethylformamide (DMF, 30 mL) at ambient temperature followed by sodium thiomethoxide (1.32 g, 17.9 mmol). Heat at 50° C. for 8 hours and dilute with water (10 mL) and diethyl ether (100 mL). Separate the layers, wash the organics with brine, and dry with magnesium sulfate before concentrating to a residue. Chromatograph the residue on a SiO2 column eluting with diethyl ether (20%) in hexane to give 566 mg (14%) of 5-bromo-1,3-dimethyl-2-methylsulfanyl-benzene. Separate the layers wash the organics with brine dry with magnesium sulfate before concentrating to a residue Chromatograph the residue on a SiO2 column eluting with diethyl ether (20%) in hexane

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

Procedure: Dissolve 5-bromo-1,3-dimethyl-2-methylsulfanyl-benzene (555 mg, 2.42 mmol) in methanol (30 mL) and treat with oxone (6.0 g, 9.8 mmol). Stir the mixture at ambient temperature for 1 hour. Filter the suspension through silica gel and elute with CH2Cl2 (100 mL). Evaporate the filtrate to give 316 mg (50%) of the title compound. Filter the suspension through silica gel elute with CH2Cl2 (100 mL) Evaporate the filtrate

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add 5-bromo-2-fluoro-1,3-dimethyl-benzene (3.5 g, 17.2 mmol) to dimethylformamide (DMF, 30 mL) at ambient temperature followed by sodium thiomethoxide (1.32 g, 17.9 mmol). Heat at 50° C. for 8 hours and dilute with water (10 mL) and diethyl ether (100 mL). Separate the layers, wash the organics with brine, and dry with magnesium sulfate before concentrating to a residue. Chromatograph the residue on a SiO2 column eluting with diethyl ether (20%) in hexane to give 566 mg (14%) of 5-bromo-1,3-dimethyl-2-methylsulfanyl-benzene. Separate the layers wash the organics with brine dry with magnesium sulfate before concentrating to a residue Chromatograph the residue on a SiO2 column eluting with diethyl ether (20%) in hexane