sodium bromide in acetone 16 h; Heating;

1: 1) NaNH2 / 1) toluene, 50 deg C, 3h, 2) 50 deg C, 3h 2: 92 percent / diethyl ether / 1) 16h, RT, 2) 1h, reflux 3: 1) NaBH4, BF3*OEt2, 2) 3N NaOH, 30percent H2O2 / 1) THF, 0 deg C, 1.5h, 2) RT, 2h 4: 40 percent / NEt3 / CH2Cl2 / 1= 0 deg C, 1h, 2) RT, 16h 5: 76 percent / NaBr / acetone / 16 h / Heating View Scheme

1: 1) NaBH4, BF3*OEt2, 2) 3N NaOH, 30percent H2O2 / 1) THF, 0 deg C, 1.5h, 2) RT, 2h 2: 40 percent / NEt3 / CH2Cl2 / 1= 0 deg C, 1h, 2) RT, 16h 3: 76 percent / NaBr / acetone / 16 h / Heating View Scheme

1: 40 percent / NEt3 / CH2Cl2 / 1= 0 deg C, 1h, 2) RT, 16h 2: 76 percent / NaBr / acetone / 16 h / Heating View Scheme

1: 92 percent / diethyl ether / 1) 16h, RT, 2) 1h, reflux 2: 1) NaBH4, BF3*OEt2, 2) 3N NaOH, 30percent H2O2 / 1) THF, 0 deg C, 1.5h, 2) RT, 2h 3: 40 percent / NEt3 / CH2Cl2 / 1= 0 deg C, 1h, 2) RT, 16h 4: 76 percent / NaBr / acetone / 16 h / Heating View Scheme

1: 95 percent / Na2CO3 / ethanol / 96 h / Heating 2: 62 percent / hexane / 0.83 h / Irradiation 3: 83 percent / m-chloroperbenzoic acid / CH2Cl2 / 3 h / 20 °C 4: 72 percent / dimethylsulfoxide-d6 / 0.02 h / 25 - 200 °C / Irradiation 5: 82 percent / H2 / Pd/C / ethyl acetate / 3 h / 20 °C / atmospheric pressure View Scheme