lithium methylmercaptide in N,N,N',N',N'',N''-hexamethylphosphoric triamide T=160°C; 2 h;

in N,N,N',N',N'',N''-hexamethylphosphoric triamide T=160°C; 2 h;

1: 54 percent / Br2 / CCl4; CH2Cl2 / 0.08 h / Ambient temperature 2: 98 percent / K2CO3 / acetone / 1.5 h / Heating 3: 1.) Br2, 2.) silver trifluoroacetate in benzene / 1.) CCl4, a) irrad., reflux, 5.75 h, b) reflux, 1.5 h, 2.) CCl4, benzene, 2.5 h 4: lithium methoxide / dimethylformamide / 14 h / 90 °C 5: 92 percent / conc. HCl, H2 / 10 percent Pd/C / acetic acid 6: 98 percent / Br2 / CH2Cl2 7: 68 percent / copper bronze / 2 h / 210 °C 8: 96 percent / LiAlH4 / diethyl ether / 1 h / Heating 9: 88 percent / pyridinium chlorochromate / CH2Cl2 / 0.5 h / Ambient temperature 10: 96 percent / butyllithium / hexane; tetrahydrofuran / 0.5 h / Ambient temperature 11: 92 percent / hexamethylphosphoric acid triamide / 2 h / 160 °C View Scheme

1: 1.) Br2, 2.) silver trifluoroacetate in benzene / 1.) CCl4, a) irrad., reflux, 5.75 h, b) reflux, 1.5 h, 2.) CCl4, benzene, 2.5 h 2: lithium methoxide / dimethylformamide / 14 h / 90 °C 3: 92 percent / conc. HCl, H2 / 10 percent Pd/C / acetic acid 4: 98 percent / Br2 / CH2Cl2 5: 68 percent / copper bronze / 2 h / 210 °C 6: 96 percent / LiAlH4 / diethyl ether / 1 h / Heating 7: 88 percent / pyridinium chlorochromate / CH2Cl2 / 0.5 h / Ambient temperature 8: 96 percent / butyllithium / hexane; tetrahydrofuran / 0.5 h / Ambient temperature 9: 92 percent / hexamethylphosphoric acid triamide / 2 h / 160 °C View Scheme

1: 98 percent / K2CO3 / acetone / 1.5 h / Heating 2: 1.) Br2, 2.) silver trifluoroacetate in benzene / 1.) CCl4, a) irrad., reflux, 5.75 h, b) reflux, 1.5 h, 2.) CCl4, benzene, 2.5 h 3: lithium methoxide / dimethylformamide / 14 h / 90 °C 4: 92 percent / conc. HCl, H2 / 10 percent Pd/C / acetic acid 5: 98 percent / Br2 / CH2Cl2 6: 68 percent / copper bronze / 2 h / 210 °C 7: 96 percent / LiAlH4 / diethyl ether / 1 h / Heating 8: 88 percent / pyridinium chlorochromate / CH2Cl2 / 0.5 h / Ambient temperature 9: 96 percent / butyllithium / hexane; tetrahydrofuran / 0.5 h / Ambient temperature 10: 92 percent / hexamethylphosphoric acid triamide / 2 h / 160 °C View Scheme

1: lithium methoxide / dimethylformamide / 14 h / 90 °C 2: 92 percent / conc. HCl, H2 / 10 percent Pd/C / acetic acid 3: 98 percent / Br2 / CH2Cl2 4: 68 percent / copper bronze / 2 h / 210 °C 5: 96 percent / LiAlH4 / diethyl ether / 1 h / Heating 6: 88 percent / pyridinium chlorochromate / CH2Cl2 / 0.5 h / Ambient temperature 7: 96 percent / butyllithium / hexane; tetrahydrofuran / 0.5 h / Ambient temperature 8: 92 percent / hexamethylphosphoric acid triamide / 2 h / 160 °C View Scheme

1: 92 percent / conc. HCl, H2 / 10 percent Pd/C / acetic acid 2: 98 percent / Br2 / CH2Cl2 3: 68 percent / copper bronze / 2 h / 210 °C 4: 96 percent / LiAlH4 / diethyl ether / 1 h / Heating 5: 88 percent / pyridinium chlorochromate / CH2Cl2 / 0.5 h / Ambient temperature 6: 96 percent / butyllithium / hexane; tetrahydrofuran / 0.5 h / Ambient temperature 7: 92 percent / hexamethylphosphoric acid triamide / 2 h / 160 °C View Scheme

1: 96 percent / butyllithium / hexane; tetrahydrofuran / 0.5 h / Ambient temperature 2: 92 percent / hexamethylphosphoric acid triamide / 2 h / 160 °C View Scheme

1: 88 percent / pyridinium chlorochromate / CH2Cl2 / 0.5 h / Ambient temperature 2: 96 percent / butyllithium / hexane; tetrahydrofuran / 0.5 h / Ambient temperature 3: 92 percent / hexamethylphosphoric acid triamide / 2 h / 160 °C View Scheme

1: 96 percent / LiAlH4 / diethyl ether / 1 h / Heating 2: 88 percent / pyridinium chlorochromate / CH2Cl2 / 0.5 h / Ambient temperature 3: 96 percent / butyllithium / hexane; tetrahydrofuran / 0.5 h / Ambient temperature 4: 92 percent / hexamethylphosphoric acid triamide / 2 h / 160 °C View Scheme