hydrogen fluoride in benzene 1.) RT, 0.5 h, 2.) 50 deg C, 10 min; Title compound not separated from byproducts;

1: 75 percent / AlCl3 / CS2 / 1 h / Ambient temperature 2: 1.) Mg / 2.) ether, 2.) ether, reflux, 4 h 3: 85 percent / BBr3 / CH2Cl2 / 1 h / Ambient temperature 4: KOH / ethanol / 20 h / Heating View Scheme

1: 62 percent / Na2S2O4*H2O / ethanol / Heating 2: 1.) conc. aq. HCl, NaNO2 / 1.) H2O, 20 min, 2.) H2O, RT, 0.5 h 3: 37 percent / 40percent aq. HF / benzene / 1.) RT, 0.5 h, 2.) 50 deg C, 10 min 4: 1.) Mg / 2.) ether, 2.) ether, reflux, 4 h 5: 85 percent / BBr3 / CH2Cl2 / 1 h / Ambient temperature 6: KOH / ethanol / 20 h / Heating View Scheme

1: 1.) Mg / 2.) ether, 2.) ether, reflux, 4 h 2: 85 percent / BBr3 / CH2Cl2 / 1 h / Ambient temperature 3: KOH / ethanol / 20 h / Heating View Scheme

1: 1.) conc. aq. HCl, NaNO2 / 1.) H2O, 20 min, 2.) H2O, RT, 0.5 h 2: 37 percent / 40percent aq. HF / benzene / 1.) RT, 0.5 h, 2.) 50 deg C, 10 min 3: 1.) Mg / 2.) ether, 2.) ether, reflux, 4 h 4: 85 percent / BBr3 / CH2Cl2 / 1 h / Ambient temperature 5: KOH / ethanol / 20 h / Heating View Scheme

1: 6N aq. HCl / 1 h / Heating 2: 1.) conc. aq. HCl, NaNO2 / 1.) H2O, 20 min, 2.) H2O, RT, 0.5 h 3: 37 percent / 40percent aq. HF / benzene / 1.) RT, 0.5 h, 2.) 50 deg C, 10 min 4: 1.) Mg / 2.) ether, 2.) ether, reflux, 4 h 5: 85 percent / BBr3 / CH2Cl2 / 1 h / Ambient temperature 6: KOH / ethanol / 20 h / Heating View Scheme

1: 75 percent / AlCl3 / CS2 / 1 h / Ambient temperature 2: 1.) Mg / 2.) ether, 2.) ether, reflux, 4 h 3: 85 percent / BBr3 / CH2Cl2 / 1 h / Ambient temperature 4: KOH / ethanol / 20 h / Heating View Scheme

1: 72 percent / AlCl3 / CS2 / 1 h / Ambient temperature 2: 62 percent / Na2S2O4*H2O / ethanol / Heating 3: 1.) conc. aq. HCl, NaNO2 / 1.) H2O, 20 min, 2.) H2O, RT, 0.5 h 4: 37 percent / 40percent aq. HF / benzene / 1.) RT, 0.5 h, 2.) 50 deg C, 10 min 5: 1.) Mg / 2.) ether, 2.) ether, reflux, 4 h 6: 85 percent / BBr3 / CH2Cl2 / 1 h / Ambient temperature 7: KOH / ethanol / 20 h / Heating View Scheme

1: 37 percent / 40percent aq. HF / benzene / 1.) RT, 0.5 h, 2.) 50 deg C, 10 min 2: 1.) Mg / 2.) ether, 2.) ether, reflux, 4 h 3: 85 percent / BBr3 / CH2Cl2 / 1 h / Ambient temperature 4: KOH / ethanol / 20 h / Heating View Scheme

1: 58 percent / PBN3 / CH2Cl2 / Ambient temperature 2: 1.) Mg / 2.) ether, 2.) ether, reflux, 4 h 3: 85 percent / BBr3 / CH2Cl2 / 1 h / Ambient temperature 4: KOH / ethanol / 20 h / Heating View Scheme