boron tribromide in dichloromethane 0.333333 h; Ambient temperature;

1: 1.) NaH / 1.) DMSO, r.t., 10 min, 2.) r.t., 1 h 2: 1.) lithium diisopropylamide, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) -78 deg C, 1 h, then -15 deg C, 30 min 3: 88 percent / p-toluenesulfonic acid / benzene / 1 h / Heating 4: 88 percent / hydrogen / 10 percent Pd-C / acetone / 6 h / 2574.3 Torr / Ambient temperature 5: 96 percent / boron tribromide / CH2Cl2 / 0.33 h / Ambient temperature View Scheme

1: 75 percent / 2 h / 140 °C 2: 1.) potassium tert-butoxide / 1.) THF-DMSO, 2.) r.t., occasional sonication, 50 min 3: 85 percent / hydrogen / 10 percent Pd-C / ethanol / 24 h / 2942.03 Torr / Ambient temperature 4: 1.) DMSO, oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 15 min, 2.) -78 deg C, 5 min, then r.t., 20 min 5: 1.) lithium diisopropylamide, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) -78 deg C, 1 h, then -15 deg C, 30 min 6: 88 percent / p-toluenesulfonic acid / benzene / 1 h / Heating 7: 88 percent / hydrogen / 10 percent Pd-C / acetone / 6 h / 2574.3 Torr / Ambient temperature 8: 96 percent / boron tribromide / CH2Cl2 / 0.33 h / Ambient temperature View Scheme

1: 1.) lithium diisopropylamide, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) -78 deg C, 1 h, then -15 deg C, 30 min 2: 88 percent / p-toluenesulfonic acid / benzene / 1 h / Heating 3: 88 percent / hydrogen / 10 percent Pd-C / acetone / 6 h / 2574.3 Torr / Ambient temperature 4: 96 percent / boron tribromide / CH2Cl2 / 0.33 h / Ambient temperature View Scheme

1: 88 percent / N-bromosuccinimide, triphenylphosphine / tetrahydrofuran / 2 h / Ambient temperature 2: 75 percent / 2 h / 140 °C 3: 1.) potassium tert-butoxide / 1.) THF-DMSO, 2.) r.t., occasional sonication, 50 min 4: 85 percent / hydrogen / 10 percent Pd-C / ethanol / 24 h / 2942.03 Torr / Ambient temperature 5: 1.) DMSO, oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 15 min, 2.) -78 deg C, 5 min, then r.t., 20 min 6: 1.) lithium diisopropylamide, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) -78 deg C, 1 h, then -15 deg C, 30 min 7: 88 percent / p-toluenesulfonic acid / benzene / 1 h / Heating 8: 88 percent / hydrogen / 10 percent Pd-C / acetone / 6 h / 2574.3 Torr / Ambient temperature 9: 96 percent / boron tribromide / CH2Cl2 / 0.33 h / Ambient temperature View Scheme

1: 1.) DMSO, oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 15 min, 2.) -78 deg C, 5 min, then r.t., 20 min 2: 1.) lithium diisopropylamide, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) -78 deg C, 1 h, then -15 deg C, 30 min 3: 88 percent / p-toluenesulfonic acid / benzene / 1 h / Heating 4: 88 percent / hydrogen / 10 percent Pd-C / acetone / 6 h / 2574.3 Torr / Ambient temperature 5: 96 percent / boron tribromide / CH2Cl2 / 0.33 h / Ambient temperature View Scheme

1: 1.) lithium diisopropylamide, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) -78 deg C, 1 h, then -15 deg C, 30 min 2: 88 percent / p-toluenesulfonic acid / benzene / 1 h / Heating 3: 88 percent / hydrogen / 10 percent Pd-C / acetone / 6 h / 2574.3 Torr / Ambient temperature 4: 96 percent / boron tribromide / CH2Cl2 / 0.33 h / Ambient temperature View Scheme

1: 85 percent / hydrogen / 10 percent Pd-C / ethanol / 24 h / 2942.03 Torr / Ambient temperature 2: 1.) DMSO, oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 15 min, 2.) -78 deg C, 5 min, then r.t., 20 min 3: 1.) lithium diisopropylamide, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) -78 deg C, 1 h, then -15 deg C, 30 min 4: 88 percent / p-toluenesulfonic acid / benzene / 1 h / Heating 5: 88 percent / hydrogen / 10 percent Pd-C / acetone / 6 h / 2574.3 Torr / Ambient temperature 6: 96 percent / boron tribromide / CH2Cl2 / 0.33 h / Ambient temperature View Scheme

1: 88 percent / hydrogen / 10 percent Pd-C / acetone / 6 h / 2574.3 Torr / Ambient temperature 2: 96 percent / boron tribromide / CH2Cl2 / 0.33 h / Ambient temperature View Scheme

1: 88 percent / p-toluenesulfonic acid / benzene / 1 h / Heating 2: 88 percent / hydrogen / 10 percent Pd-C / acetone / 6 h / 2574.3 Torr / Ambient temperature 3: 96 percent / boron tribromide / CH2Cl2 / 0.33 h / Ambient temperature View Scheme