N-bromosuccinmide; triphenylphosphine in tetrahydrofuran 2 h; Ambient temperature;

sodium hydride in tetrahydrofuran 24 h; Ambient temperature;

magnesium oxide; lithium trifluoromethane sulfonate; lithium tetrakis(pentafluorophenyl)-borate in dichloromethane; cyclohexane T=20°C; 24 h;

4-(bromomethylene)morpholin-4-ium bromide in dichloromethane T=0°C; 1 h; Inert atmosphere;

sodium in diethyl ether Heating;

sodium bromide in acetone 5 h; Heating;

1: 1.) 60percent NaH / 1.) C6H6, r.t., 30 min, 2.) C6H6, reflux, 4 h 2: 95 percent / pyridine / 12 h / Ambient temperature 3: 93 percent / NaBr / acetone / 5 h / Heating View Scheme

1: 1.) 60percent NaH / 1.) C6H6, r.t., 30 min, 2.) C6H6, reflux, 4 h 2: 95 percent / pyridine / 12 h / Ambient temperature 3: 93 percent / NaBr / acetone / 5 h / Heating View Scheme

1: 1.) NaH 2: 100 percent / aq. KOH / methanol / 5 h / Heating 3: 83 percent / diethyl phosphorocyanidate, Et3N / dimethylformamide / 2 h / 0 °C 4: 100 percent / aq. KOH / methanol / 10 h / Heating 5: 87 percent / NBS / dimethylformamide / 24 h / Ambient temperature 6: 6N aq. HCl / 12 h / Heating 7: diethyl ether 8: 98 percent / K2CO3 / 6 h / Ambient temperature View Scheme

1: 75 percent / 2 h / 140 °C 2: 1.) potassium tert-butoxide / 1.) THF-DMSO, 2.) r.t., occasional sonication, 50 min 3: 93 percent / hydrogen / 10 percent Pd-C / ethanol / 24 h / 2942.03 Torr / Ambient temperature View Scheme