1: 82 percent / LAH 2: 92 percent / PBr3 / pyridine 3: 80 percent / NaOMe / dimethylformamide 4: 80 percent / BBr3 View Scheme

1.1: SOCl2 2.1: Et3N / tetrahydrofuran / 0 °C 3.1: silver benzoate; Et3N / methanol 3.2: aq. KOH / methanol View Scheme

1: 65 percent / SOCl2 / benzene / 5 h / Heating 2: 77 percent / (Et)3N / CH2Cl2 / 1.) 0 deg C, 2 h, 2.) RT, overnight 3: 96 percent / 47percent HBr / methanol; CHCl3 / 0.17 h / -10 °C View Scheme

1: thionyl chloride / benzene / 1 h / Heating 2: Et3N / diethyl ether / 4 h 3: 86 percent / silver benzoate, Et3N / 1 h / Heating 4: 55 percent / AcOH, perchloric acid (3 drops) / 0.25 h / Ambient temperature 5: NaH / tetrahydrofuran / 2 h / Ambient temperature 6: tetrahydrofuran / 0.5 h 7: 27 percent / ethanol / 1 h / Irradiation 8: 9 percent / KOH (40percent) / ethanol; dioxane / 2.5 h / Heating 9: 65 percent / potassium dichromate / dioxane; acetic acid / 5 h / Ambient temperature 10: 28 percent / MnO2, H2SO4 (conc.) / 0.5 h / 60 °C 11: silver oxide / dioxane / 1.5 h / Ambient temperature View Scheme

1: 82 percent / LAH 2: 92 percent / PBr3 / pyridine View Scheme

lithium aluminium tetrahydride

thionyl chloride in benzene 5 h; Heating;

1: 82 percent / LAH 2: 92 percent / PBr3 / pyridine 3: 80 percent / NaOMe / dimethylformamide View Scheme

1: 3,5-bis(phenylmethoxy)benzoic acid With oxalyl dichloride in dichloromethane T=20°C; 6 h; 2: 3-amino-1-methyl-pyrazole in dichloromethane T=20°C; 16 h;

1.1: 1-methyl-imidazole; p-toluenesulfonyl chloride / acetonitrile 1.2: acetonitrile 2.1: 85 percent / Amberlyst(R) 15 / ethanol; H2O / Heating View Scheme