phosphorus tribromide in toluene T=100°C; 0.25 h;

N-bromosuccinmide; meta-chloroperoxybenzoic acid in tetrachloromethane 6 h; Heating;

1: boron dimethyl-trifluoro sulphide / tetrahydrofuran / 0 - 60 °C / Inert atmosphere 2: phosphorus tribromide / toluene / 0.25 h / 100 °C View Scheme

1: sodium tetrahydroborate / methanol / 1 h / 0 - 5 °C / Inert atmosphere 2: phosphorus tribromide / toluene / 0.5 h / 40 - 100 °C / Inert atmosphere View Scheme

1: 5 h / Heating 2: 83 percent / NaH / 1,2-dimethoxy-ethane / 2 h / Heating 3: 82 percent / H2, morpholine / 5 percent Rh/C / ethanol; methanol / 4 h / 18100.2 Torr / Ambient temperature 4: 81 percent / HCOONa / 3 h / Heating 5: K2CO3, Cu, CuBr / dimethylsulfoxide / 3 h / 160 °C 6: 5 N aq. NaOH / dimethylsulfoxide / 0.5 h / 75 °C View Scheme

1,3,5,7-tetra-azatricyclo[5.1.1.13,5]decane in acetic acid 4 h; Heating;

in dimethyl sulfoxide Ambient temperature;

tetra-(n-butyl)ammonium iodide; potassium carbonate in N,N-dimethyl-formamide 2.5 h;