carbon tetrabromide; tris-(dimethylamino)-phosphine in dichloromethane T=20°C; 16 h;

1: Et3N / tetrahydrofuran 2: dimethylsulfoxide / 60 °C 3: NaOH / methanol / Heating 4: 56 percent / LiAlH4 / tetrahydrofuran / 3 h / 20 °C 5: 24 percent / CBr4; tris(dimethylamino)phosphine / CH2Cl2 / 16 h / 20 °C View Scheme

1: NaOH / methanol / Heating 2: 56 percent / LiAlH4 / tetrahydrofuran / 3 h / 20 °C 3: 24 percent / CBr4; tris(dimethylamino)phosphine / CH2Cl2 / 16 h / 20 °C View Scheme

1: LiAlH4 / tetrahydrofuran 2: Et3N / tetrahydrofuran 3: dimethylsulfoxide / 60 °C 4: NaOH / methanol / Heating 5: 56 percent / LiAlH4 / tetrahydrofuran / 3 h / 20 °C 6: 24 percent / CBr4; tris(dimethylamino)phosphine / CH2Cl2 / 16 h / 20 °C View Scheme

1: 56 percent / LiAlH4 / tetrahydrofuran / 3 h / 20 °C 2: 24 percent / CBr4; tris(dimethylamino)phosphine / CH2Cl2 / 16 h / 20 °C View Scheme

sodium hydride in N,N-dimethyl-formamide T=0 - 20°C; 0.583333 h;