sodium carbonate in diethyl ether; water T=25°C; 1 h;

1: 74 percent / SOCl2 / Heating 2: 93 percent / aq. Na2CO3 / diethyl ether / 3 h / 25 °C View Scheme

1: 67 percent / AlCl3 / nitrobenzene / 6 h / 100 °C 2: 74 percent / SOCl2 / Heating 3: 93 percent / aq. Na2CO3 / diethyl ether / 3 h / 25 °C View Scheme

tetra-(n-butyl)ammonium iodide; potassium carbonate in N,N-dimethyl-formamide T=23°C; 6 h; Yields of byproduct given. Title compound not separated from byproducts;

tetra-(n-butyl)ammonium iodide; potassium carbonate in N,N-dimethyl-formamide T=20°C; 6 h;

1: 60 percent / K2CO3; (n-Bu)4NI / dimethylformamide / 6 h / 20 °C 2: mCPBA / CH2Cl2 / 40 °C 3: 453 mg / NH3 / CH2Cl2; methanol / 1 h 4: 61 percent / K2CO3 / dimethylformamide / 6 h / 25 °C 5: H2 / Pd/C / CH2Cl2 6: aq. Na2CO3 / acetonitrile View Scheme

1: 60 percent / K2CO3; (n-Bu)4NI / dimethylformamide / 6 h / 20 °C 2: mCPBA / CH2Cl2 / 40 °C 3: 453 mg / NH3 / CH2Cl2; methanol / 1 h 4: H2 / Pd/C / CH2Cl2 View Scheme

1: 60 percent / K2CO3; (n-Bu)4NI / dimethylformamide / 6 h / 20 °C 2: mCPBA / CH2Cl2 / 40 °C 3: 453 mg / NH3 / CH2Cl2; methanol / 1 h View Scheme

1: 89 percent / NaH / tetrahydrofuran; dimethylformamide / 6 h / Heating 2: m-chloroperbenzoic acid (mCPBA) / CH2Cl2 / 24 h / 40 °C 3: HCl / methanol / 3 h / 25 °C 4: H2 / 10percent Pd/C / methanol / 6 h / 25 °C 5: EDCI, HOBt*H2O / dimethylformamide / 16 h / 25 °C 6: 1.) NaH, CuBr-SMe2 / 1.) collidine, 25 deg C, 0.5 h, 2.) collidine, 130 deg C, 9 h 7: 98 percent / H2 / 10percent Pd/C / tetrahydrofuran / 6 h / 25 °C 8: 53 percent / EDCI, HOBt*H2O / dimethylformamide / 12 h / 25 °C 9: aq. LiOH / tetrahydrofuran; methanol / 2 h / 25 °C 10: 3 N HCl / ethyl acetate / 1 h / 25 °C 11: 58 percent / NaHCO3, diphenyl phosphoroazidate (DPPA) / dimethylformamide / 72 h / 0 °C 12: 57 percent / BBr3 / CH2Cl2 / 3 h / -78 - 20 °C View Scheme

1: 89 percent / NaH / tetrahydrofuran; dimethylformamide / 6 h / Heating 2: m-chloroperbenzoic acid (mCPBA) / CH2Cl2 / 24 h / 40 °C 3: HCl / methanol / 3 h / 25 °C 4: H2 / 10percent Pd/C / methanol / 6 h / 25 °C 5: EDCI, HOBt*H2O / dimethylformamide / 16 h / 25 °C 6: 1.) NaH, CuBr-SMe2 / 1.) collidine, 25 deg C, 0.5 h, 2.) collidine, 130 deg C, 9 h 7: 98 percent / H2 / 10percent Pd/C / tetrahydrofuran / 6 h / 25 °C 8: 53 percent / EDCI, HOBt*H2O / dimethylformamide / 12 h / 25 °C 9: aq. LiOH / tetrahydrofuran; methanol / 2 h / 25 °C 10: 3 N HCl / ethyl acetate / 1 h / 25 °C 11: 58 percent / NaHCO3, diphenyl phosphoroazidate (DPPA) / dimethylformamide / 72 h / 0 °C View Scheme