1,3-difluoro-2-methylsulfanylbenzene

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Combine 1,3-difluoro-2-methylsulfanyl-benzene (4.3 g, 27 mmol), iron (300 mg, 5.4 mmol), bromine (1.4 mL, 27 mmol), aluminium chloride (400 mg, 3.0 mmol) and dichloromethane (100 mL), at 0° C. Stir the reaction mixture at room temperature for 2 hours. Add saturated sodium thiosulfate solution (20 mL) and diethyl ether (100 mL). Separate the layers and wash the organic layer with brine (20 mL). Dry with MgSO4, filter and concentrate in vacuo. Chromatograph the residue on a column eluting the material with diethyl ether in hexane (0 to 5%) to give 1.1 g of 5-bromo-1,3-difluoro-2-methylsulfanyl-benzene (17%). at 0° C Separate the layers wash the organic layer with brine (20 mL) Dry with MgSO4 filter concentrate in vacuo Chromatograph the residue on a column eluting the material with diethyl ether in hexane (0 to 5%)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Combine 1,3-difluoro-2-methylsulfanyl-benzene (4.3 g, 27 mmol), iron (300 mg, 5.4 mmol), bromine (1.4 mL, 27 mmol), aluminium chloride (400 mg, 3.0 mmol) and dichloromethane (100 mL), at 0° C. Stir the reaction mixture at room temperature for 2 hours. Add saturated sodium thiosulfate solution (20 mL) and diethyl ether (100 mL). Separate the layers and wash the organic layer with brine (20 mL). Dry with MgSO4, filter and concentrate in vacuo. Chromatograph the residue on a column eluting the material with diethyl ether in hexane (0 to 5%) to give 1.1 g of 5-bromo-1,3-difluoro-2-methylsulfanyl-benzene (17%). at 0° C Separate the layers wash the organic layer with brine (20 mL) Dry with MgSO4 filter concentrate in vacuo Chromatograph the residue on a column eluting the material with diethyl ether in hexane (0 to 5%)

反応条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Dissolve 1,3-difluorobenzene (3.5 g, 30.7 mmol) into THF (100 mL). Cool the mixture to −78° C. and add n-butyl lithium (19 mL, 30.7 mmol). Stir for 20 minutes and add dimethyldisulfide (3 mL, 3.38 mmol). Remove the cooling bath and warm to room temperature. Pour the reaction mixture into ice (10 g) and add diethyl ether (100 mL). Separate the layers and wash the organic layer with brine (20 mL). Dry with MgSO4, filter, and concentrate in vacuo to give 4.3 g of 1,3-difluoro-2-methylsulfanyl-benzene (88%). Remove the cooling bath warm to room temperature Pour the reaction mixture into ice (10 g) add diethyl ether (100 mL) Separate the layers wash the organic layer with brine (20 mL) Dry with MgSO4 filter concentrate in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Combine 1,3-difluoro-2-methylsulfanyl-benzene (4.3 g, 27 mmol), iron (300 mg, 5.4 mmol), bromine (1.4 mL, 27 mmol), aluminium chloride (400 mg, 3.0 mmol) and dichloromethane (100 mL), at 0° C. Stir the reaction mixture at room temperature for 2 hours. Add saturated sodium thiosulfate solution (20 mL) and diethyl ether (100 mL). Separate the layers and wash the organic layer with brine (20 mL). Dry with MgSO4, filter and concentrate in vacuo. Chromatograph the residue on a column eluting the material with diethyl ether in hexane (0 to 5%) to give 1.1 g of 5-bromo-1,3-difluoro-2-methylsulfanyl-benzene (17%). at 0° C Separate the layers wash the organic layer with brine (20 mL) Dry with MgSO4 filter concentrate in vacuo Chromatograph the residue on a column eluting the material with diethyl ether in hexane (0 to 5%)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Combine 1,3-difluoro-2-methylsulfanyl-benzene (4.3 g, 27 mmol), iron (300 mg, 5.4 mmol), bromine (1.4 mL, 27 mmol), aluminium chloride (400 mg, 3.0 mmol) and dichloromethane (100 mL), at 0° C. Stir the reaction mixture at room temperature for 2 hours. Add saturated sodium thiosulfate solution (20 mL) and diethyl ether (100 mL). Separate the layers and wash the organic layer with brine (20 mL). Dry with MgSO4, filter and concentrate in vacuo. Chromatograph the residue on a column eluting the material with diethyl ether in hexane (0 to 5%) to give 1.1 g of 5-bromo-1,3-difluoro-2-methylsulfanyl-benzene (17%). at 0° C Separate the layers wash the organic layer with brine (20 mL) Dry with MgSO4 filter concentrate in vacuo Chromatograph the residue on a column eluting the material with diethyl ether in hexane (0 to 5%)

反応条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Dissolve 1,3-difluorobenzene (3.5 g, 30.7 mmol) into THF (100 mL). Cool the mixture to −78° C. and add n-butyl lithium (19 mL, 30.7 mmol). Stir for 20 minutes and add dimethyldisulfide (3 mL, 3.38 mmol). Remove the cooling bath and warm to room temperature. Pour the reaction mixture into ice (10 g) and add diethyl ether (100 mL). Separate the layers and wash the organic layer with brine (20 mL). Dry with MgSO4, filter, and concentrate in vacuo to give 4.3 g of 1,3-difluoro-2-methylsulfanyl-benzene (88%). Remove the cooling bath warm to room temperature Pour the reaction mixture into ice (10 g) add diethyl ether (100 mL) Separate the layers wash the organic layer with brine (20 mL) Dry with MgSO4 filter concentrate in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Combine 1,3-difluoro-2-methylsulfanyl-benzene (4.3 g, 27 mmol), iron (300 mg, 5.4 mmol), bromine (1.4 mL, 27 mmol), aluminium chloride (400 mg, 3.0 mmol) and dichloromethane (100 mL), at 0° C. Stir the reaction mixture at room temperature for 2 hours. Add saturated sodium thiosulfate solution (20 mL) and diethyl ether (100 mL). Separate the layers and wash the organic layer with brine (20 mL). Dry with MgSO4, filter and concentrate in vacuo. Chromatograph the residue on a column eluting the material with diethyl ether in hexane (0 to 5%) to give 1.1 g of 5-bromo-1,3-difluoro-2-methylsulfanyl-benzene (17%). at 0° C Separate the layers wash the organic layer with brine (20 mL) Dry with MgSO4 filter concentrate in vacuo Chromatograph the residue on a column eluting the material with diethyl ether in hexane (0 to 5%)

反応条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Dissolve 1,3-difluorobenzene (3.5 g, 30.7 mmol) into THF (100 mL). Cool the mixture to −78° C. and add n-butyl lithium (19 mL, 30.7 mmol). Stir for 20 minutes and add dimethyldisulfide (3 mL, 3.38 mmol). Remove the cooling bath and warm to room temperature. Pour the reaction mixture into ice (10 g) and add diethyl ether (100 mL). Separate the layers and wash the organic layer with brine (20 mL). Dry with MgSO4, filter, and concentrate in vacuo to give 4.3 g of 1,3-difluoro-2-methylsulfanyl-benzene (88%). Remove the cooling bath warm to room temperature Pour the reaction mixture into ice (10 g) add diethyl ether (100 mL) Separate the layers wash the organic layer with brine (20 mL) Dry with MgSO4 filter concentrate in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Combine 1,3-difluoro-2-methylsulfanyl-benzene (4.3 g, 27 mmol), iron (300 mg, 5.4 mmol), bromine (1.4 mL, 27 mmol), aluminium chloride (400 mg, 3.0 mmol) and dichloromethane (100 mL), at 0° C. Stir the reaction mixture at room temperature for 2 hours. Add saturated sodium thiosulfate solution (20 mL) and diethyl ether (100 mL). Separate the layers and wash the organic layer with brine (20 mL). Dry with MgSO4, filter and concentrate in vacuo. Chromatograph the residue on a column eluting the material with diethyl ether in hexane (0 to 5%) to give 1.1 g of 5-bromo-1,3-difluoro-2-methylsulfanyl-benzene (17%). at 0° C Separate the layers wash the organic layer with brine (20 mL) Dry with MgSO4 filter concentrate in vacuo Chromatograph the residue on a column eluting the material with diethyl ether in hexane (0 to 5%)

反応条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Dissolve 1,3-difluorobenzene (3.5 g, 30.7 mmol) into THF (100 mL). Cool the mixture to −78° C. and add n-butyl lithium (19 mL, 30.7 mmol). Stir for 20 minutes and add dimethyldisulfide (3 mL, 3.38 mmol). Remove the cooling bath and warm to room temperature. Pour the reaction mixture into ice (10 g) and add diethyl ether (100 mL). Separate the layers and wash the organic layer with brine (20 mL). Dry with MgSO4, filter, and concentrate in vacuo to give 4.3 g of 1,3-difluoro-2-methylsulfanyl-benzene (88%). Remove the cooling bath warm to room temperature Pour the reaction mixture into ice (10 g) add diethyl ether (100 mL) Separate the layers wash the organic layer with brine (20 mL) Dry with MgSO4 filter concentrate in vacuo