N-bromosuccinmide in tetrachloromethane; water

N-bromosuccinmide; dibenzoyl peroxide in tetrachloromethane 8 h; Heating;

N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile in tetrachloromethane Heating / reflux;

1: triethylamine / dichloromethane / 0.17 h / 0 °C 2: ammonium hydroxide / 0.03 h / 0 °C 3: 2,4,6-trichloro-1,3,5-triazine / 0 - 20 °C 4: N-bromosuccinmide; dibenzoyl peroxide / tetrachloromethane / 16 h / Reflux; Inert atmosphere View Scheme

1: 2,4,6-trichloro-1,3,5-triazine / 0 - 20 °C 2: N-bromosuccinmide; dibenzoyl peroxide / tetrachloromethane / 16 h / Reflux; Inert atmosphere View Scheme

1.1: N,N-dimethyl-formamide / 18 h / 90 °C / Inert atmosphere 2.1: water; sodium hydroxide / methanol / 4 h 3.1: toluene-4-sulfonic acid / dichloromethane / 15 h / 20 °C / Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran / 0.17 h / -98 °C / Inert atmosphere 4.2: 1.67 h / -98 - 20 °C / Inert atmosphere 5.1: water / tetrahydrofuran / 1 h / 20 °C 6.1: magnesium sulfate / dichloromethane / 15 h / 20 °C / Inert atmosphere 7.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / diethyl ether / -78 °C / Inert atmosphere 7.2: -98 - -78 °C / Inert atmosphere 8.1: toluene-4-sulfonic acid / diethyl ether / Inert atmosphere; Reflux 9.1: water; sodium tris(acetoxy)borohydride; acetic acid / dichloromethane / 16 h / 20 °C View Scheme

1.1: N,N-dimethyl-formamide / 18 h / 90 °C / Inert atmosphere 2.1: water; sodium hydroxide / methanol / 4 h 3.1: toluene-4-sulfonic acid / dichloromethane / 15 h / 20 °C / Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran / 0.17 h / -98 °C / Inert atmosphere 4.2: 1.67 h / -98 - 20 °C / Inert atmosphere 5.1: water / tetrahydrofuran / 1 h / 20 °C 6.1: magnesium sulfate / dichloromethane / 15 h / 20 °C / Inert atmosphere 7.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / diethyl ether / -78 °C / Inert atmosphere 7.2: -98 - -78 °C / Inert atmosphere 8.1: toluene-4-sulfonic acid / diethyl ether / Inert atmosphere; Reflux View Scheme

1: 77 percent / dimethylformamide / 16 h / 20 °C 2: 80 percent / DIBAL-H / tetrahydrofuran; hexane / 3 h / 20 °C View Scheme

1: dimethylformamide / 80 °C 2: 4.63 g / aq. NaOH / methanol / 1 h / 20 °C View Scheme