N-bromosuccinmide in N,N-dimethyl-formamide T=0 - 20°C;

1: 33 percent / ammonia / methanol / 20 °C 2: 92 percent / N-bromosuccinimide / dimethylformamide / 0 - 20 °C View Scheme

1: 59 percent / PdCl2(dppf)*CH2Cl2 / tetrahydrofuran / 4 h / Heating 2: 43 percent / SbBr3; t-BuONO / various solvent(s) / 6 h / 4 - 10 °C 3: 38 percent / sodium methoxide; pyridine / 3 h / Heating View Scheme