hydrogen iodide in acetonitrile T=60°C; 1.5 h;

1: 98 percent / i-pentyl nitrite; HOAc / 0 - 5 °C 2: 95 percent / aq. NaOH / 0.5 h / 0 - 5 °C 3: 71 percent / aq. HI / acetonitrile / 1.5 h / 60 °C View Scheme

isopropylmagnesium chloride in tetrahydrofuran; toluene T=-35 - -25°C; 2 h; Inert atmosphere;

1: 1,3-dibromo-5-fluoro-2-iodobenzene With isopropylmagnesium chloride in tetrahydrofuran Inert atmosphere; 2: N,N-dimethyl-formamide in tetrahydrofuran; water Inert atmosphere;