1: K2CO3 / CHCl3 2: dichloroacetic acid 4: H2 / Pd/C / methanol 5: 65 percent / chloranil / xylene / 150 °C 6: 70 percent / di-isobutyl aluminiumhydride / tetrahydrofuran / 0 °C 7: 55 percent / DCC, dimethylaminopyridine / diethyl ether 8: 52 percent / AgO / dioxane; aq. HNO3 View Scheme

1: 91 percent / triethylamine / diethyl ether / 3 h / Ambient temperature 2: 55 percent / polyphosphate ester / 9.5 h / 110 - 120 °C 3: 60 percent / decalin / 5 percent Pd/C / 3 h / 160 - 170 °C 4: 83 percent / Me2AlNH2 / benzene / 36 h / Heating 5: H2, conc. HCl / 5 percent Pd/C / methanol 6: 1,1-dichlorodimethyl ether / 0.5 h / 60 °C 7: 53 percent / 6 M HNO3; silver oxide / dioxane / 0.25 h / Ambient temperature View Scheme

boron tribromide in dichloromethane