boron tribromide in dichloromethane T=0 - 20°C; 0.333333 h;

1: 96 percent / NH4NO3 / ethanol / 24 h 2: 30 percent / K2CO3, CuO / pyridine / 48 h / Heating 3: 73 percent / AlCl3 / benzene / 24 h 4: 60 percent / K2CO3 / dimethylformamide / 1 h / 120 °C 5: NaBH4 / ethanol 6: PBr3 / benzene / 2 h / Ambient temperature 7: 84 percent / acetonitrile / 1 h / Heating 8: 1) NaOMe, 2) H2 / 2) palladium-charcoal / 1) methylene dichloride, methanol, 1h, 2) ethyl acetate, methanol 9: 91 percent / K2CO3 / acetone / 6 h / Heating 10: 100 percent / PBr3 / benzene / 80 °C 11: 15 percent / sodium, tetraphenylethene / tetrahydrofuran / 24 h View Scheme

1: 30 percent / K2CO3, CuO / pyridine / 48 h / Heating 2: 73 percent / AlCl3 / benzene / 24 h 3: 60 percent / K2CO3 / dimethylformamide / 1 h / 120 °C 4: NaBH4 / ethanol 5: PBr3 / benzene / 2 h / Ambient temperature 6: 84 percent / acetonitrile / 1 h / Heating 7: 1) NaOMe, 2) H2 / 2) palladium-charcoal / 1) methylene dichloride, methanol, 1h, 2) ethyl acetate, methanol 8: 91 percent / K2CO3 / acetone / 6 h / Heating 9: 100 percent / PBr3 / benzene / 80 °C 10: 15 percent / sodium, tetraphenylethene / tetrahydrofuran / 24 h View Scheme

2: 63 percent / pyridine / 24 h 3: 17 percent / Ph3P / NiCl2(Ph3P)2, Zn / dimethylformamide / 18 h 4: 1) NaOMe, 2) H2 / 2) palladium-charcoal / 1) methylene dichloride, methanol, 1h, 2) ethyl acetate, methanol 5: 91 percent / K2CO3 / acetone / 6 h / Heating 6: 100 percent / PBr3 / benzene / 80 °C 7: 15 percent / sodium, tetraphenylethene / tetrahydrofuran / 24 h View Scheme

1: SOCl2 / 1 h / Heating 2: 63 percent / pyridine / 24 h 3: 17 percent / Ph3P / NiCl2(Ph3P)2, Zn / dimethylformamide / 18 h 4: 1) NaOMe, 2) H2 / 2) palladium-charcoal / 1) methylene dichloride, methanol, 1h, 2) ethyl acetate, methanol 5: 91 percent / K2CO3 / acetone / 6 h / Heating 6: 100 percent / PBr3 / benzene / 80 °C 7: 15 percent / sodium, tetraphenylethene / tetrahydrofuran / 24 h View Scheme

1: 73 percent / AlCl3 / benzene / 24 h 2: 60 percent / K2CO3 / dimethylformamide / 1 h / 120 °C 3: NaBH4 / ethanol 4: PBr3 / benzene / 2 h / Ambient temperature 5: 84 percent / acetonitrile / 1 h / Heating 6: 1) NaOMe, 2) H2 / 2) palladium-charcoal / 1) methylene dichloride, methanol, 1h, 2) ethyl acetate, methanol 7: 91 percent / K2CO3 / acetone / 6 h / Heating 8: 100 percent / PBr3 / benzene / 80 °C 9: 15 percent / sodium, tetraphenylethene / tetrahydrofuran / 24 h View Scheme

1: 63 percent / pyridine / 24 h 2: 17 percent / Ph3P / NiCl2(Ph3P)2, Zn / dimethylformamide / 18 h 3: 1) NaOMe, 2) H2 / 2) palladium-charcoal / 1) methylene dichloride, methanol, 1h, 2) ethyl acetate, methanol 4: 91 percent / K2CO3 / acetone / 6 h / Heating 5: 100 percent / PBr3 / benzene / 80 °C 6: 15 percent / sodium, tetraphenylethene / tetrahydrofuran / 24 h View Scheme

1: 1) NaOMe, 2) H2 / 2) palladium-charcoal / 1) methylene dichloride, methanol, 1h, 2) ethyl acetate, methanol 2: 91 percent / K2CO3 / acetone / 6 h / Heating 3: 100 percent / PBr3 / benzene / 80 °C 4: 15 percent / sodium, tetraphenylethene / tetrahydrofuran / 24 h View Scheme

1: 17 percent / Ph3P / NiCl2(Ph3P)2, Zn / dimethylformamide / 18 h 2: 1) NaOMe, 2) H2 / 2) palladium-charcoal / 1) methylene dichloride, methanol, 1h, 2) ethyl acetate, methanol 3: 91 percent / K2CO3 / acetone / 6 h / Heating 4: 100 percent / PBr3 / benzene / 80 °C 5: 15 percent / sodium, tetraphenylethene / tetrahydrofuran / 24 h View Scheme

1: NaBH4 / ethanol 2: PBr3 / benzene / 2 h / Ambient temperature 3: 84 percent / acetonitrile / 1 h / Heating 4: 1) NaOMe, 2) H2 / 2) palladium-charcoal / 1) methylene dichloride, methanol, 1h, 2) ethyl acetate, methanol 5: 91 percent / K2CO3 / acetone / 6 h / Heating 6: 100 percent / PBr3 / benzene / 80 °C 7: 15 percent / sodium, tetraphenylethene / tetrahydrofuran / 24 h View Scheme