(2-benzylsulfanylphenyl)methanol

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

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

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

Procedure: A solution of (2-Benzylsulfanyl)methanol 4 (120 mg, 0.522 mmol) in anhydrous Et2O was cooled to 4° C. A solution of PBr3 (49 μL, 0.52 mmol) in anhydrous Et2O was added dropwise, keeping the temperature below 10° C. The reaction was allowed to warm to ambient temperature and stirred for one hour. The reaction was filtered through silica gel (2.0 g) and washed with Et2O. The filtrate was washed with H2O saturated aqueous sodium bicarbonate and brine. The organic layer was dried over Na2SO4, filtered and evaporated to give 95 mg of the named product as a yellow oil. the temperature below 10° C The reaction was filtered through silica gel (2.0 g) washed with Et2O The filtrate was washed with H2O saturated aqueous sodium bicarbonate and brine The organic layer was dried over Na2SO4 filtered evaporated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-benzylsulfanyl benzoic acid 3 (50 mg, 0.206 mmol) in THF at 0° C. was added LiAlH4 (0.62 mL of a 1.0 mL solution in THF, 0.62 mmol) and the mixture was stirred at 0° C. for 15 minutes then allowed to warm to room temperature. The solution was stirred for 2 hours. The mixture was cooled at 0° C. then methanol (MeOH) was added slowly followed by HCl (0.5N) and tetrahydrofuran (THF). The mixture was stirred at room temperature for 30 minutes. It was then concentrated to remove THF, extracted with CH2Cl2 (3×), dried over MgSO4, filtered and concentrated to give 30 mg of the product as a yellow oil. to warm to room temperature The solution was stirred for 2 hours The mixture was cooled at 0° C. The mixture was stirred at room temperature for 30 minutes It was then concentrated to remove THF extracted with CH2Cl2 (3×) dried over MgSO4 filtered concentrated

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

Procedure: A solution of (2-Benzylsulfanyl)methanol 4 (120 mg, 0.522 mmol) in anhydrous Et2O was cooled to 4° C. A solution of PBr3 (49 μL, 0.52 mmol) in anhydrous Et2O was added dropwise, keeping the temperature below 10° C. The reaction was allowed to warm to ambient temperature and stirred for one hour. The reaction was filtered through silica gel (2.0 g) and washed with Et2O. The filtrate was washed with H2O saturated aqueous sodium bicarbonate and brine. The organic layer was dried over Na2SO4, filtered and evaporated to give 95 mg of the named product as a yellow oil. the temperature below 10° C The reaction was filtered through silica gel (2.0 g) washed with Et2O The filtrate was washed with H2O saturated aqueous sodium bicarbonate and brine The organic layer was dried over Na2SO4 filtered evaporated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-benzylsulfanyl benzoic acid 3 (50 mg, 0.206 mmol) in THF at 0° C. was added LiAlH4 (0.62 mL of a 1.0 mL solution in THF, 0.62 mmol) and the mixture was stirred at 0° C. for 15 minutes then allowed to warm to room temperature. The solution was stirred for 2 hours. The mixture was cooled at 0° C. then methanol (MeOH) was added slowly followed by HCl (0.5N) and tetrahydrofuran (THF). The mixture was stirred at room temperature for 30 minutes. It was then concentrated to remove THF, extracted with CH2Cl2 (3X), dried over MgSO4, filtered and concentrated to give 30 mg of the product as a yellow oil. to warm to room temperature The solution was stirred for 2 hours The mixture was cooled at 0° C. The mixture was stirred at room temperature for 30 minutes It was then concentrated to remove THF extracted with CH2Cl2 (3X) dried over MgSO4 filtered concentrated

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

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

Procedure: A solution of (2-Benzylsulfanyl)methanol 4 (120 mg, 0.522 mmol) in anhydrous Et2O was cooled to 4° C. A solution of PBr3 (49 μL, 0.52 mmol) in anhydrous Et2O was added dropwise, keeping the temperature below 10° C. The reaction was allowed to warm to ambient temperature and stirred for one hour. The reaction was filtered through silica gel (2.0 g) and washed with Et2O. The filtrate was washed with H2O saturated aqueous sodium bicarbonate and brine. The organic layer was dried over Na2SO4, filtered and evaporated to give 95 mg of the named product as a yellow oil. the temperature below 10° C The reaction was filtered through silica gel (2.0 g) washed with Et2O The filtrate was washed with H2O saturated aqueous sodium bicarbonate and brine The organic layer was dried over Na2SO4 filtered evaporated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-benzylsulfanyl benzoic acid 3 (50 mg, 0.206 mmol) in THF at 0° C. was added LiAlH4 (0.62 mL of a 1.0 mL solution in THF, 0.62 mmol) and the mixture was stirred at 0° C. for 15 minutes then allowed to warm to room temperature. The solution was stirred for 2 hours. The mixture was cooled at 0° C. then methanol (MeOH) was added slowly followed by HCl (0.5N) and tetrahydrofuran (THF). The mixture was stirred at room temperature for 30 minutes. It was then concentrated to remove THF, extracted with CH2Cl2 (3X), dried over MgSO4, filtered and concentrated to give 30 mg of the product as a yellow oil. to warm to room temperature The solution was stirred for 2 hours The mixture was cooled at 0° C. The mixture was stirred at room temperature for 30 minutes It was then concentrated to remove THF extracted with CH2Cl2 (3X) dried over MgSO4 filtered concentrated

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

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

Procedure: A solution of (2-Benzylsulfanyl) methanol 4 (120 mg, 0.522 mmol) in anhydrous Et2O was cooled to 4° C. A solution of PBr3 (49 μL, 0.52 mmol) in anhydrous Et2O was added dropwise, keeping the temperature below 10° C. The reaction was allowed to warm to ambient temperature and stirred for one hour. The reaction was filtered through silica gel (2.0 g) and washed with Et2O. The filtrate was washed with H2O saturated aqueous sodium bicarbonate and brine. The organic layer was dried over Na2SO4, filtered and evaporated to give 95 mg of the named product as a yellow oil. the temperature below 10° C The reaction was filtered through silica gel (2.0 g) washed with Et2O The filtrate was washed with H2O saturated aqueous sodium bicarbonate and brine The organic layer was dried over Na2SO4 filtered evaporated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-benzylsulfanyl benzoic acid 3 (50 mg, 0.206 mmol) in THF at 0° C. was added LiAlH4 (0.62 mL of a 1.0 mL solution in THF, 0.62 mmol) and the mixture was stirred at 0° C. for 15 minutes then allowed to warm to room temperature. The solution was stirred for 2 hours. The mixture was cooled at 0° C. then methanol (MeOH) was added slowly followed by HCl (0.5N) and tetrahydrofuran (THF). The mixture was stirred at room temperature for 30 minutes. It was then concentrated to remove THF, extracted with CH2Cl2 (3×), dried over MgSO4, filtered and concentrated to give 30 mg of the product as a yellow oil. to warm to room temperature The solution was stirred for 2 hours The mixture was cooled at 0° C. The mixture was stirred at room temperature for 30 minutes It was then concentrated to remove THF extracted with CH2Cl2 (3×) dried over MgSO4 filtered concentrated