boron tribromide in dichloromethane T=-80 - 20°C; 13 h;

boron tribromide in dichloromethane T=-70 - 20°C; 48 h;

1: 88 percent / potassium carbonate / dimethylformamide / 0.17 h / 160 °C 2: 87 percent / KOH / ethanol / 50 °C 3: 1.)Tl(NO3)3*3H2O, 2.)Na2SO3, 5percent HCl / 1.) CHCl3, 30 deg C, 24 h 2.) 0 deg C 4: H2 / 10percent Pd/C / methanol; ethyl acetate / Ambient temperature 5: 68 percent / aq 10percent HCl / methanol / Heating 6: 96 percent / pyridine / Heating 7: 1.) AlCl3 2.)aq HCl / 1.) MeCN, 70 deg C, 2.) MeCN,50-60 deg C, 30 min View Scheme

1: 87 percent / KOH / ethanol / 50 °C 2: 1.)Tl(NO3)3*3H2O, 2.)Na2SO3, 5percent HCl / 1.) CHCl3, 30 deg C, 24 h 2.) 0 deg C 3: H2 / 10percent Pd/C / methanol; ethyl acetate / Ambient temperature 4: 68 percent / aq 10percent HCl / methanol / Heating 5: 96 percent / pyridine / Heating 6: 1.) AlCl3 2.)aq HCl / 1.) MeCN, 70 deg C, 2.) MeCN,50-60 deg C, 30 min View Scheme

1: 1.)Tl(NO3)3*3H2O, 2.)Na2SO3, 5percent HCl / 1.) CHCl3, 30 deg C, 24 h 2.) 0 deg C 2: H2 / 10percent Pd/C / methanol; ethyl acetate / Ambient temperature 3: 68 percent / aq 10percent HCl / methanol / Heating 4: 96 percent / pyridine / Heating 5: 1.) AlCl3 2.)aq HCl / 1.) MeCN, 70 deg C, 2.) MeCN,50-60 deg C, 30 min View Scheme

1.1: 72 percent / BF3*OEt2 / 0.25 h / Heating 2.1: formic acid / tetrahydrofuran / 1 h / 0 °C 2.2: 72 percent / tetrahydrofuran / 12.5 h / 0 - 100 °C 3.1: 79 percent / BBr3 / CH2Cl2 / 13 h / -80 - 20 °C View Scheme

1.1: 72 percent / BF3*OEt2 / 0.25 h / Heating 2.1: formic acid / tetrahydrofuran / 1 h / 0 °C 2.2: 72 percent / tetrahydrofuran / 12.5 h / 0 - 100 °C 3.1: 79 percent / BBr3 / CH2Cl2 / 13 h / -80 - 20 °C View Scheme

1: 96 percent / pyridine / Heating 2: 1.) AlCl3 2.)aq HCl / 1.) MeCN, 70 deg C, 2.) MeCN,50-60 deg C, 30 min View Scheme

1: 68 percent / aq 10percent HCl / methanol / Heating 2: 96 percent / pyridine / Heating 3: 1.) AlCl3 2.)aq HCl / 1.) MeCN, 70 deg C, 2.) MeCN,50-60 deg C, 30 min View Scheme

Micrococcus or Arthrobacter 48 h; Yield given. Yields of byproduct given;