tetrabutyl ammonium fluoride; triethylamine; cesium fluoride in tetrahydrofuran T=70°C;

1: AgF / acetonitrile; H2O / 20 h / 80 °C 2: 1.) KOH, 2.) aq. HCl / 1.) MeOH, 25 deg C, 30 min, 2.) dioxane, hot water bath, 10 min View Scheme

1: 1.) red phosphorus, bromine / 1.) 80 deg C, 12 h, 2.) 0 deg C --> 80 deg C, 60 min 2: AgF / acetonitrile; H2O / 20 h / 80 °C 3: 1.) KOH, 2.) aq. HCl / 1.) MeOH, 25 deg C, 30 min, 2.) dioxane, hot water bath, 10 min View Scheme

(i) NaH, DMF, (ii) /BRN= 773989/, (iii) aq. HCl, dioxane; Multistep reaction;