1: 90 percent / mercuric bromide, mercuric cyanide, 4A molecular sieves / acetonitrile / 1 h / Ambient temperature 2: 78 percent / 60 percent acetic acid / H2O / 0.5 h / 80 °C / Heating 3: 67 percent / mercuric bromide, mercuric cyanide, 4A molecular sieves / acetonitrile / 1 h / Ambient temperature 4: 1.) acetic acid, sodium acetate; 2.) methanol / 1.) 10 percent palladium-on-charcoal; 2.) 2 M sodium methoxide / 1.) ethanol, water, heating for 17 h at 75 deg C; 2.) 30 min View Scheme

1: 76 percent / 50 percent sodium hydroxide / tetra-butylammonium hydrogen sulfate / CH2Cl2; H2O / 20 h / Heating 2: 90 percent / mercuric bromide, mercuric cyanide, 4A molecular sieves / acetonitrile / 1 h / Ambient temperature 3: 78 percent / 60 percent acetic acid / H2O / 0.5 h / 80 °C / Heating 4: 67 percent / mercuric bromide, mercuric cyanide, 4A molecular sieves / acetonitrile / 1 h / Ambient temperature 5: 1.) acetic acid, sodium acetate; 2.) methanol / 1.) 10 percent palladium-on-charcoal; 2.) 2 M sodium methoxide / 1.) ethanol, water, heating for 17 h at 75 deg C; 2.) 30 min View Scheme

sodium methylate in methanol Substitution;

1: Et3N / CH2Cl2 2: SOCl2 3: Bu2SnO / Microwave irradiation 4: 73 percent / p-TsOH 5: 48 percent / NIS; TfOAg / CH2Cl2 / 0 °C 6: 55 percent / NIS; TfOAg / CH2Cl2 / -20 °C 7: NaOMe / methanol View Scheme

1: SOCl2 2: Bu2SnO / Microwave irradiation 3: 73 percent / p-TsOH 4: 48 percent / NIS; TfOAg / CH2Cl2 / 0 °C 5: 55 percent / NIS; TfOAg / CH2Cl2 / -20 °C 6: NaOMe / methanol View Scheme

1: Bu2SnO / Microwave irradiation 2: 73 percent / p-TsOH 3: 48 percent / NIS; TfOAg / CH2Cl2 / 0 °C 4: 55 percent / NIS; TfOAg / CH2Cl2 / -20 °C 5: NaOMe / methanol View Scheme

1: 55 percent / NIS; TfOAg / CH2Cl2 / -20 °C 2: NaOMe / methanol View Scheme

1: 48 percent / NIS; TfOAg / CH2Cl2 / 0 °C 2: 55 percent / NIS; TfOAg / CH2Cl2 / -20 °C 3: NaOMe / methanol View Scheme

1: 73 percent / p-TsOH 2: 48 percent / NIS; TfOAg / CH2Cl2 / 0 °C 3: 55 percent / NIS; TfOAg / CH2Cl2 / -20 °C 4: NaOMe / methanol View Scheme

methanol; sodium acetate; acetic acid; palladium on activated charcoal; sodium methylate 1.) ethanol, water, heating for 17 h at 75 deg C; 2.) 30 min; Yield given. Multistep reaction;