pyridine-2-carboxylic acid, Ag(II) salt in water; benzene Ambient temperature;

1: 85 percent / HBr / acetic acid / 20 h / Ambient temperature 2: 94 percent / bromine / CCl4 / 168 h 3: 87 percent / potassium phenylselenite, dipotassium hydrogen phosphate, 18-crown-6 / acetonitrile / 22 h / Heating 4: 97 percent / toluene-p-sulfonic acid / benzene / 3 h / Heating 5: 1.) n-BuLi, CuI, (CH3)2Se / 1.) THF, hexane -78 deg C, 3 h 2.) THF, hexane -78 deg C 70 min then rt 1 h 6: HCl / H2O; tetrahydrofuran; hexane / 15 h / Ambient temperature 7: 93 percent / NaOH, TEBA / tetrahydrofuran / 4 h / Ambient temperature 8: 62 percent / silver(II) dipicolinate / benzene; H2O / Ambient temperature View Scheme

1: 97 percent / toluene-p-sulfonic acid / benzene / 3 h / Heating 2: 1.) n-BuLi, CuI, (CH3)2Se / 1.) THF, hexane -78 deg C, 3 h 2.) THF, hexane -78 deg C 70 min then rt 1 h 3: HCl / H2O; tetrahydrofuran; hexane / 15 h / Ambient temperature 4: 93 percent / NaOH, TEBA / tetrahydrofuran / 4 h / Ambient temperature 5: 62 percent / silver(II) dipicolinate / benzene; H2O / Ambient temperature View Scheme

1: 93 percent / NaOH, TEBA / tetrahydrofuran / 4 h / Ambient temperature 2: 62 percent / silver(II) dipicolinate / benzene; H2O / Ambient temperature View Scheme

1: 1.) n-BuLi, CuI, (CH3)2Se / 1.) THF, hexane -78 deg C, 3 h 2.) THF, hexane -78 deg C 70 min then rt 1 h 2: HCl / H2O; tetrahydrofuran; hexane / 15 h / Ambient temperature 3: 93 percent / NaOH, TEBA / tetrahydrofuran / 4 h / Ambient temperature 4: 62 percent / silver(II) dipicolinate / benzene; H2O / Ambient temperature View Scheme