tetrabutyl ammonium fluoride

tetrafluoroboric acid; sodium nitrite in water T=0 - 20°C; Balz-Schiemann reaction; 22 h;

1.1: AcCl; NaI / acetonitrile / Heating 1.2: 52 percent / aq. NaOH / tetrahydrofuran / 40 °C 2.1: 99 percent / NaH / tetrahydrofuran / Heating 3.1: n-butyllithium / diethyl ether / -78 °C 3.2: 71 percent / N-fluorobenzenesulfonimide / tetrahydrofuran / -78 °C 4.1: 100 percent / TBAF / tetrahydrofuran / 20 °C View Scheme

1: 13.15 g / methanesulfonic acid / Pd/C / ethanol / 72 h / 105 °C 2: 44 percent / tetrafluoroboric acid; sodium nitrite / H2O / 22 h / 0 - 20 °C View Scheme

1.1: n-butyllithium / diethyl ether / -78 °C 1.2: 66 percent / N-fluorobenzenesulfonimide / tetrahydrofuran / -78 °C 2.1: 100 percent / TBAF / tetrahydrofuran / 20 °C View Scheme

1.1: 54 percent / tetramethylammonium bromide; methanesulfonic anhydride / dimethylformamide / 4 h / 0 - 23 °C 2.1: 99 percent / sodium hydride / tetrahydrofuran / 3 h / 80 °C 3.1: tert-butyllithium / tetrahydrofuran; pentane / 0.08 h / -78 °C 3.2: 84 percent / N-fluorobenzenesulfonimide / pentane; tetrahydrofuran / 0.75 h / -78 °C 4.1: 100 percent / tetrabutylammonium fluoride View Scheme

1.1: 99 percent / sodium hydride / tetrahydrofuran / 3 h / 80 °C 2.1: tert-butyllithium / tetrahydrofuran; pentane / 0.08 h / -78 °C 2.2: 84 percent / N-fluorobenzenesulfonimide / pentane; tetrahydrofuran / 0.75 h / -78 °C 3.1: 100 percent / tetrabutylammonium fluoride View Scheme

1.1: 99 percent / NaH / tetrahydrofuran / Heating 2.1: n-butyllithium / diethyl ether / -78 °C 2.2: 71 percent / N-fluorobenzenesulfonimide / tetrahydrofuran / -78 °C 3.1: 100 percent / TBAF / tetrahydrofuran / 20 °C View Scheme

1.1: n-butyllithium / diethyl ether / -78 °C 1.2: 71 percent / N-fluorobenzenesulfonimide / tetrahydrofuran / -78 °C 2.1: 100 percent / TBAF / tetrahydrofuran / 20 °C View Scheme

nitric acid T=0°C; 0.166667 h;