hydrogenchloride in tetrahydrofuran; water 2 h; Heating;

tert-butylhypochlorite in chloroform; benzene 1) 0 deg C, 2 h, 2) r.t., overnight;

1: 88 percent / ZnCl2, 85percent H3PO4 / toluene / Heating 2: 60 percent / t-butyl hypochlorite / benzene; CHCl3 / 1) 0 deg C, 2 h, 2) r.t., overnight View Scheme

1: 94 percent / conc. HCl / tetrahydrofuran; H2O / 2 h / Heating 2: 77 percent / ammoniumacetate, / acetic acid; benzene / 30 h / Heating View Scheme

1: 94 percent / conc. HCl / tetrahydrofuran; H2O / 2 h / Heating 2: 77 percent / ammoniumacetate, / acetic acid; benzene / 30 h / Heating 3: 73 percent / NaOH / H2O / 0.17 h / 65 °C 4: 87 percent / iodine / ethanol / 24 h / Heating 5: 49 percent / Cu powder / quinoline / 1 h / 180 °C 6: 54 percent / pyridine / 3 h / Heating 7: 1) benzoyl peroxide, NBS / 1) CCl4, reflux, 10 h, 2) DMSO 8: 81 percent / K2CO3 / acetone / 18 h / Heating 9: 1) borane/dimethyl sulfide, 2) 1.0 M HCl / 1) THF, 45 min, reflux, 2) CH3OH, reflux 10: 87 percent / sodium acetate / H2O / 0.5 h View Scheme