1: HCl gas / methanol / 1) 0 deg C, 1 h, 2) 0 deg C to rt, 1.5 h 2: K2CO3 / acetone / 12 h / Heating 3: 49 percent / Et3N, Ph3P / Pd(OAc)2 / 17 h / 80 °C 4: 95 percent / H2 / Pd/C / ethanol / 4 h 5: 86 percent / (COCl)2 / CH2Cl2; dimethylsulfoxide / 1 h / -78 °C 6: 63 percent / NaNH2 / tetrahydrofuran / 2 h / -78 °C 7: 93 percent / 48percent HBr / ethanol / 1 h 8: 91 percent / Ag2CO3 / benzene / 2 h View Scheme