1: With thionyl chloride; N,N-dimethyl-formamide in toluene T=50°C; 4 h; 2: With ammonia in water; toluene

ammonia in water; toluene

1.1: N-bromosuccinmide / methanol / -5 - 0 °C 2.1: hydrogenchloride / water; tetrahydrofuran / 0.5 h / 0 °C 2.2: 2 h / 0 °C 2.3: 20 °C 3.1: thionyl chloride / N,N-dimethyl-formamide / toluene / 4 h / 50 °C 4.1: ammonia / toluene View Scheme

1.1: hydrogenchloride / water; tetrahydrofuran / 0.5 h / 0 °C 1.2: 2 h / 0 °C 1.3: 20 °C 2.1: thionyl chloride / N,N-dimethyl-formamide / toluene / 4 h / 50 °C 3.1: ammonia / toluene View Scheme

dimethylsulfide borane complex in tetrahydrofuran T=0°C; Reflux;