N-bromosuccinmide in acetonitrile

1: With palladium 10 on activated carbon; hydrogen in ethyl acetate T=20°C; P=258.581 Torr; 15 h; Large scale; 2: With 1,3-dibromo-5,5-dimethyl-hydantoin in ethyl acetate T=15°C; 12 h; Large scale;

sodium tetrahydroborate; 2,2'-azo-bisisobutyronitrile; 1-{6-[dibutyl(chloro)stannyl]hexyl}-3-methyl-1H-imidazolium iodide in methanol; acetonitrile T=80°C; 22 h; Inert atmosphere;

1: 84 percent / n-BuLi / tetrahydrofuran / -78 - 25 °C 2: 60 percent / 100percent HNO3 / acetic anhydride; acetic acid / 1.25 h / 0 °C 3: 83 percent / H2 / Pd/C / methanol / 2.5 h / 25 °C 4: 1.) O2; 2.) trimethylamine N-oxide / 1.) MeCN, 25 deg C, 6 d; 2.) acetone, 56 deg C, 4 h 5: Pd/C / xylene / 4 h / 145 °C View Scheme

1: 6-bromo-2,3-dimethoxy toluene With methyl-magnesium chloride; magnesium in tetrahydrofuran T=25°C; Inert atmosphereLarge scale; 2: carbon dioxide in tetrahydrofuran; water T=-60°C; Inert atmosphereLarge scale; 3: With sulfuric acid in tetrahydrofuran; water T=25 - 30°C; 1 h; Inert atmosphereLarge scale;

1.1: BuLi / tetrahydrofuran / -78 °C 1.2: 86 percent / tetrahydrofuran / -78 - 25 °C 2.1: 76 percent / HNO3 / acetic anhydride; acetic acid / 0 °C 3.1: 96 percent / H2 / 10 percent Pd/C / methanol 4.1: air / acetonitrile / 120 h / 25 °C 4.2: Me3NO / acetone / 4.5 h / 56 °C 4.3: 65 percent / 10 percent Pd/C / xylene / 4 h / 145 °C View Scheme

n-butyllithium in tetrahydrofuran