phosphorus tribromide in diethyl ether 16 h; Ambient temperature;

1: 83.7 percent / H2 / 5percent Pd/C / ethanol / 760 Torr 2: 88.6 percent / LiAlH4 / tetrahydrofuran 3: 51.6 percent / PBr3 / diethyl ether; diethyl ether / 16 h / Ambient temperature View Scheme

1: 70.1 percent / NaH / benzene 2: 83.7 percent / H2 / 5percent Pd/C / ethanol / 760 Torr 3: 88.6 percent / LiAlH4 / tetrahydrofuran 4: 51.6 percent / PBr3 / diethyl ether; diethyl ether / 16 h / Ambient temperature View Scheme

1: 88.6 percent / LiAlH4 / tetrahydrofuran 2: 51.6 percent / PBr3 / diethyl ether; diethyl ether / 16 h / Ambient temperature View Scheme