1: 89.6 percent / sodium methylate / ethanol; methanol / 5 h / Heating 2: 89.2 percent / phosphorus oxychloride, N,N-dimethylaniline / 1 h / Heating 3: 90.8 percent / methanol / 5 h / Heating 4: 71.7 percent / N-bromosuccinimide, dibenzoylperoxide, α,α'-azoisobutyronitrile / CCl4 / 3 h / Heating; Irradiation 5: 61 percent / sodium, 2-nitropropane / ethanol / 2 h / 60 - 65 °C View Scheme

sodium hypobromide; lithium bromide in dimethyl sulfoxide 1 h;

1: 38 percent / NaOBr, LiBr / dimethylsulfoxide / 1 h 2: 74 percent / molten tetrabutylammonium fluoride / 4 h / 25 °C View Scheme

1: 12 percent / NaOCl / H2O; diethyl ether / 0.08 h / cooling 2: 95 percent / t-BuOCl / CH2Cl2 / 24 h / 0 °C 3: LiBr / acetonitrile / 0.17 h / 20 °C View Scheme