hydrogenchloride in chloroform; water; 3-chloro-benzenecarboperoxoic acid

sodium tetrahydroborate in methanol T=0°C; 24 h;

1: 94 percent / pyridine / 0.25 h / 0 °C 2: 61 percent / phenyliodine(III) bis(trifluoroacetate) / 2,2,2-trifluoro-ethanol / 0.17 h / -40 °C 3: 95 percent / BCl3 / CH2Cl2 / 20 h / -78 °C 4: 83 percent / pyridine / 3 h / 0 °C 5: 98 percent / formic acid; Et3N; PPh3 / Pd(OAc)2 / dimethylformamide / 72 h / 60 °C 6: 78 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 3 h / -78 °C 7: 96 percent / TBAB; KOH / methanol / 24 h / 80 °C 8: NaBH4 / methanol / 24 h / 20 °C View Scheme

1: 83 percent / pyridine / 3 h / 0 °C 2: 98 percent / formic acid; Et3N; PPh3 / Pd(OAc)2 / dimethylformamide / 72 h / 60 °C 3: 78 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 3 h / -78 °C 4: 96 percent / TBAB; KOH / methanol / 24 h / 80 °C 5: NaBH4 / methanol / 24 h / 20 °C View Scheme

1: 98 percent / formic acid; Et3N; PPh3 / Pd(OAc)2 / dimethylformamide / 72 h / 60 °C 2: 78 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 3 h / -78 °C 3: 96 percent / TBAB; KOH / methanol / 24 h / 80 °C 4: NaBH4 / methanol / 24 h / 20 °C View Scheme

1: 95 percent / BCl3 / CH2Cl2 / 20 h / -78 °C 2: 83 percent / pyridine / 3 h / 0 °C 3: 98 percent / formic acid; Et3N; PPh3 / Pd(OAc)2 / dimethylformamide / 72 h / 60 °C 4: 78 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 3 h / -78 °C 5: 96 percent / TBAB; KOH / methanol / 24 h / 80 °C 6: NaBH4 / methanol / 24 h / 20 °C View Scheme

1: 61 percent / phenyliodine(III) bis(trifluoroacetate) / 2,2,2-trifluoro-ethanol / 0.17 h / -40 °C 2: 95 percent / BCl3 / CH2Cl2 / 20 h / -78 °C 3: 83 percent / pyridine / 3 h / 0 °C 4: 98 percent / formic acid; Et3N; PPh3 / Pd(OAc)2 / dimethylformamide / 72 h / 60 °C 5: 78 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 3 h / -78 °C 6: 96 percent / TBAB; KOH / methanol / 24 h / 80 °C 7: NaBH4 / methanol / 24 h / 20 °C View Scheme

iron(II) sulfate in methanol T=10°C; 1.5 h;

1: With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid in dichloromethane; water T=0°C; 0.5 h; 2: With iron(II) sulfate in methanol; dichloromethane; water T=-10 - 0°C; 3 h;

1: 96 percent / TBAB; KOH / methanol / 24 h / 80 °C 2: NaBH4 / methanol / 24 h / 20 °C View Scheme