oxalyl dichloride; dimethyl sulfoxide; triethylamine 1.) CH2Cl2, -60 deg C, 1 h, 2.) CH2Cl2, from -60 deg C to RT, 1 h; Yield given. Multistep reaction;

tetrakis(triphenylphosphine) palladium(0); water; sodium carbonate in 1,4-dioxane T=80°C; Suzuki cross-coupling; Inert atmosphere;

1: 82 percent / K2CO3 / methanol / 3.5 h / Heating 2: 87 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 5 °C 3: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C, 1 h, 2.) CH2Cl2, from -60 deg C to RT, 1 h View Scheme

1: 87 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 5 °C 2: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C, 1 h, 2.) CH2Cl2, from -60 deg C to RT, 1 h View Scheme