1: With boron trichloride in dichloromethane T=0°C; Inert atmosphere; 2: With water in dichloromethane

boron trichloride in dichloromethane T=-78 - 20°C; Inert atmosphere;

hydrogenchloride in tetrahydrofuran 2 h; Heating;

1: 88 percent / sodium acetate, H2 / 10percent Pd/C / benzene; acetic anhydride / 24 h 2: 65 percent / pyridine / 12 h 3: 48 mg / N-bromosuccinimide (NBS), benzoyl peroxide / CCl4 / 0.33 h / Heating 4: 34 mg / LiBr, Li2CO3, hydroquinone / dimethylformamide / 110 °C 5: sodium methoxide / methanol View Scheme

1: 1.) potassium tert-butoxide 2.) H2O, citric acid, Na2HPO4, Fremy's salt (K2ON(SO3)2) / 1.) ethanol, reflux, 3 h, 2.) RT, overnight 2: 93 percent / sodium dithionite / H2O; dioxane / 0.5 h / Ambient temperature 3: 77 percent / K2CO3, potassium tert-butoxide / dimethylformamide; tetrahydrofuran / Ambient temperature 4: 88 percent / sodium acetate, H2 / 10percent Pd/C / benzene; acetic anhydride / 24 h 5: 65 percent / pyridine / 12 h 6: 48 mg / N-bromosuccinimide (NBS), benzoyl peroxide / CCl4 / 0.33 h / Heating 7: 34 mg / LiBr, Li2CO3, hydroquinone / dimethylformamide / 110 °C 8: sodium methoxide / methanol View Scheme

1: 77 percent / K2CO3, potassium tert-butoxide / dimethylformamide; tetrahydrofuran / Ambient temperature 2: 88 percent / sodium acetate, H2 / 10percent Pd/C / benzene; acetic anhydride / 24 h 3: 65 percent / pyridine / 12 h 4: 48 mg / N-bromosuccinimide (NBS), benzoyl peroxide / CCl4 / 0.33 h / Heating 5: 34 mg / LiBr, Li2CO3, hydroquinone / dimethylformamide / 110 °C 6: sodium methoxide / methanol View Scheme

1: 93 percent / sodium dithionite / H2O; dioxane / 0.5 h / Ambient temperature 2: 77 percent / K2CO3, potassium tert-butoxide / dimethylformamide; tetrahydrofuran / Ambient temperature 3: 88 percent / sodium acetate, H2 / 10percent Pd/C / benzene; acetic anhydride / 24 h 4: 65 percent / pyridine / 12 h 5: 48 mg / N-bromosuccinimide (NBS), benzoyl peroxide / CCl4 / 0.33 h / Heating 6: 34 mg / LiBr, Li2CO3, hydroquinone / dimethylformamide / 110 °C 7: sodium methoxide / methanol View Scheme

1: 91 percent / NaH / dimethylformamide 2: 72 percent / 1.) n-BuLi; 3.) H3O(+) / tetrahydrofuran / 1.) -78 deg C 3: 95 percent / Ba(OH)2 / Pd(0) 4: 70 percent / 1.) LDA; 2.) 50percent aq. HOAc / 1.) THF, reflux, 2.5 h; 2.) reflux, 10 min 5: 81 percent / Et3N / CH2Cl2 / -78 °C 6: 69 percent / LiCl, (2-furyl)3P / Pd2(dba)3 / various solvent(s) / 5 h / Ambient temperature 7: 90 percent / BCl3 / CH2Cl2 / 0.17 h / 0 °C View Scheme

1: 72 percent / 1.) n-BuLi; 3.) H3O(+) / tetrahydrofuran / 1.) -78 deg C 2: 95 percent / Ba(OH)2 / Pd(0) 3: 70 percent / 1.) LDA; 2.) 50percent aq. HOAc / 1.) THF, reflux, 2.5 h; 2.) reflux, 10 min 4: 81 percent / Et3N / CH2Cl2 / -78 °C 5: 69 percent / LiCl, (2-furyl)3P / Pd2(dba)3 / various solvent(s) / 5 h / Ambient temperature 6: 90 percent / BCl3 / CH2Cl2 / 0.17 h / 0 °C View Scheme

1: 95 percent / Ba(OH)2 / Pd(0) 2: 70 percent / 1.) LDA; 2.) 50percent aq. HOAc / 1.) THF, reflux, 2.5 h; 2.) reflux, 10 min 3: 81 percent / Et3N / CH2Cl2 / -78 °C 4: 69 percent / LiCl, (2-furyl)3P / Pd2(dba)3 / various solvent(s) / 5 h / Ambient temperature 5: 90 percent / BCl3 / CH2Cl2 / 0.17 h / 0 °C View Scheme