1: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, RT, 12 h 2: 91 percent / H2, concd. NH4OH, NH3 (gas) / Raney nickel W-2 / methanol; tetrahydrofuran / 8 h / 2585.7 - 2844.3 Torr 3: HBr, phenol / acetic acid; CH2Cl2 / 24 h / Ambient temperature View Scheme

1: 91 percent / H2, concd. NH4OH, NH3 (gas) / Raney nickel W-2 / methanol; tetrahydrofuran / 8 h / 2585.7 - 2844.3 Torr 2: HBr, phenol / acetic acid; CH2Cl2 / 24 h / Ambient temperature View Scheme

hydrogen bromide; phenol in dichloromethane; acetic acid 24 h; Ambient temperature;