in tetrahydrofuran 1.) -78 deg C, 10 min, 2.) reflux, 5 min;

1: Et3N / diethyl ether / 2 h / Ambient temperature 2: NaBH4 / ethanol / 2 h / Heating 3: BF3*Et2O / acetone / 2 h / Heating 4: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 1 h, 2.) a) -78 deg C, 2 h, b) 0 deg C, 1 h 5: TsOH*H2O / benzene; H2O / 3 h / Heating 6: 1.) m-chloroperbenzoic acid, 2.) Et2NH / 1.) THF, -20 deg C, 20 min, 2.) CCl4, reflux, 10 min View Scheme

1: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 1 h, 2.) a) -78 deg C, 2 h, b) 0 deg C, 1 h 2: TsOH*H2O / benzene; H2O / 3 h / Heating 3: 1.) m-chloroperbenzoic acid, 2.) Et2NH / 1.) THF, -20 deg C, 20 min, 2.) CCl4, reflux, 10 min View Scheme

1: NaBH4 / ethanol / 2 h / Heating 2: BF3*Et2O / acetone / 2 h / Heating 3: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 1 h, 2.) a) -78 deg C, 2 h, b) 0 deg C, 1 h 4: TsOH*H2O / benzene; H2O / 3 h / Heating 5: 1.) m-chloroperbenzoic acid, 2.) Et2NH / 1.) THF, -20 deg C, 20 min, 2.) CCl4, reflux, 10 min View Scheme

1: BF3*Et2O / acetone / 2 h / Heating 2: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 1 h, 2.) a) -78 deg C, 2 h, b) 0 deg C, 1 h 3: TsOH*H2O / benzene; H2O / 3 h / Heating 4: 1.) m-chloroperbenzoic acid, 2.) Et2NH / 1.) THF, -20 deg C, 20 min, 2.) CCl4, reflux, 10 min View Scheme

diethylamine; 3-chloro-benzenecarboperoxoic acid 1.) THF, -20 deg C, 20 min, 2.) CCl4, reflux, 10 min; Yield given. Multistep reaction;