1: 1.) nBuLi, 2.) BF3*Et2O / 1.) hexane, THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2 h and -50 deg C, 1 h. 2: 96 percent / NaHg / methanol 3: N,N-diisopropylethylamine / CH2Cl2 / 0.25 h / 0 °C 4: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; H2O / 0.5 h / Ambient temperature 5: 1.) 2,4,6-trichlorobenzoyl chloride, Et3N, 2.) 4-dimethylaminopyridine / 1.) toluene, room temperature, 2 h, 2.) toluene, overnight. 6: 31 percent / AgNO3, phosphate buffer, N-chlorosuccinimide / acetone / 0.17 h / Ambient temperature; pH=7 8: 80 percent / pyridinium poly(hydrogen fluoride) / tetrahydrofuran / 0 °C View Scheme

1: 96 percent / BF3*Et2O / CH2Cl2 / 1.) 0 deg C, 1 h, 2.) room temperature, overnight. 2: 1.) nBuLi, 2.) BF3*Et2O / 1.) hexane, THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2 h and -50 deg C, 1 h. 3: 96 percent / NaHg / methanol 4: N,N-diisopropylethylamine / CH2Cl2 / 0.25 h / 0 °C 5: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; H2O / 0.5 h / Ambient temperature 6: 1.) 2,4,6-trichlorobenzoyl chloride, Et3N, 2.) 4-dimethylaminopyridine / 1.) toluene, room temperature, 2 h, 2.) toluene, overnight. 7: 31 percent / AgNO3, phosphate buffer, N-chlorosuccinimide / acetone / 0.17 h / Ambient temperature; pH=7 9: 80 percent / pyridinium poly(hydrogen fluoride) / tetrahydrofuran / 0 °C View Scheme

1.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 5 h / 20 °C 1.2: 84 percent / 4-(dimethylamino)pyridine / toluene / 0.5 h / 20 °C 2.1: pyridinium poly(hydrogen fluoride) / tetrahydrofuran / 12 h / 20 °C 3.1: 8.0 mg / mercury(II) perchlorate trihydrate; calcium carbonate / acetonitrile; H2O / 0.05 h / 20 °C View Scheme

1.1: HMPA; t-BuLi / tetrahydrofuran; hexane / 1.5 h / -50 - -43 °C 1.2: 87 percent / tetrahydrofuran; hexane / 1 h / -78 - -50 °C 2.1: pyridine; 4-(dimethylamino)pyridine / 20 °C 3.1: DDQ / CH2Cl2; H2O; toluene / 1 h / 20 °C 4.1: 24.7 mg / CaCO3 / methanol / 7 h / 20 °C 5.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 5 h / 20 °C 5.2: 84 percent / 4-(dimethylamino)pyridine / toluene / 0.5 h / 20 °C 6.1: pyridinium poly(hydrogen fluoride) / tetrahydrofuran / 12 h / 20 °C 7.1: 8.0 mg / mercury(II) perchlorate trihydrate; calcium carbonate / acetonitrile; H2O / 0.05 h / 20 °C View Scheme

1.1: 99 percent / 2,6-lutidine / CH2Cl2 / -20 - 20 °C 2.1: HMPA; t-BuLi / tetrahydrofuran; hexane / 1.5 h / -50 - -43 °C 2.2: 87 percent / tetrahydrofuran; hexane / 1 h / -78 - -50 °C 3.1: pyridine; 4-(dimethylamino)pyridine / 20 °C 4.1: DDQ / CH2Cl2; H2O; toluene / 1 h / 20 °C 5.1: 24.7 mg / CaCO3 / methanol / 7 h / 20 °C 6.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 5 h / 20 °C 6.2: 84 percent / 4-(dimethylamino)pyridine / toluene / 0.5 h / 20 °C 7.1: pyridinium poly(hydrogen fluoride) / tetrahydrofuran / 12 h / 20 °C 8.1: 8.0 mg / mercury(II) perchlorate trihydrate; calcium carbonate / acetonitrile; H2O / 0.05 h / 20 °C View Scheme

1.1: HMPA; t-BuLi / tetrahydrofuran; hexane / 1.5 h / -50 - -43 °C 1.2: 87 percent / tetrahydrofuran; hexane / 1 h / -78 - -50 °C 2.1: pyridine; 4-(dimethylamino)pyridine / 20 °C 3.1: DDQ / CH2Cl2; H2O; toluene / 1 h / 20 °C 4.1: 24.7 mg / CaCO3 / methanol / 7 h / 20 °C 5.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 5 h / 20 °C 5.2: 84 percent / 4-(dimethylamino)pyridine / toluene / 0.5 h / 20 °C 6.1: pyridinium poly(hydrogen fluoride) / tetrahydrofuran / 12 h / 20 °C 7.1: 8.0 mg / mercury(II) perchlorate trihydrate; calcium carbonate / acetonitrile; H2O / 0.05 h / 20 °C View Scheme

1.1: pyridine; 4-(dimethylamino)pyridine / 20 °C 2.1: DDQ / CH2Cl2; H2O; toluene / 1 h / 20 °C 3.1: 24.7 mg / CaCO3 / methanol / 7 h / 20 °C 4.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 5 h / 20 °C 4.2: 84 percent / 4-(dimethylamino)pyridine / toluene / 0.5 h / 20 °C 5.1: pyridinium poly(hydrogen fluoride) / tetrahydrofuran / 12 h / 20 °C 6.1: 8.0 mg / mercury(II) perchlorate trihydrate; calcium carbonate / acetonitrile; H2O / 0.05 h / 20 °C View Scheme

1: AcOH / H2O / 1.) overnight, 2.) 50 deg C, 2 h. 2: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 1.5 h / Ambient temperature 3: 1.) n-BuLi, 2.) TsCl / 1.) THF, 0 deg C, 10 min, 2.) THF, 0 deg C, 20 min. 4: 1.) nBuLi, 2.) BF3*Et2O / 1.) hexane, THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2 h and -50 deg C, 1 h. 5: 71 percent / Na-Hg / methanol 6: N,N-diisopropylethylamine / CH2Cl2 / 0.5 h / 0 °C 7: pyridinium p-toluenesulfonate / methanol / 1.) room temperature, overnight, 2.) 50 deg C, 1 h. 8: 1.) 2,4,6-trichlorobenzoyl chloride, Et3N, 2.) 4-dimethylaminopyridine / 1.) toluene, room temperature, 2 h, 2.) toluene, room temperature, 30 min. 9: 1.) pyridinium poly(hydrogen fluoride), 2.) Hg(ClO4)2*3H2O, CaCO3 / 1.) THF, room temperature, overnight, 2.) acetonitrile, H2O, room temperature, 5 min. View Scheme

1: 1.) 2,4,6-trichlorobenzoyl chloride, Et3N, 2.) 4-dimethylaminopyridine / 1.) toluene, room temperature, 2 h, 2.) toluene, overnight. 2: 31 percent / AgNO3, phosphate buffer, N-chlorosuccinimide / acetone / 0.17 h / Ambient temperature; pH=7 4: 80 percent / pyridinium poly(hydrogen fluoride) / tetrahydrofuran / 0 °C View Scheme

1: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; H2O / 0.5 h / Ambient temperature 2: 1.) 2,4,6-trichlorobenzoyl chloride, Et3N, 2.) 4-dimethylaminopyridine / 1.) toluene, room temperature, 2 h, 2.) toluene, overnight. 3: 31 percent / AgNO3, phosphate buffer, N-chlorosuccinimide / acetone / 0.17 h / Ambient temperature; pH=7 5: 80 percent / pyridinium poly(hydrogen fluoride) / tetrahydrofuran / 0 °C View Scheme