N-bromosuccinmide in N,N-dimethyl-formamide T=10°C; 0.0833333 h;

sodium hydroxide in methanol 1.5 h; Heating;

1: CH2Cl2 / 0.17 h / 5 °C 2: 97 percent / t-BuOK / 2 h / Heating 3: 96 percent / NBS / dimethylformamide / 4 h / 80 °C 4: 100 percent / aq. NaOH / methanol / 1.5 h / Heating View Scheme

1: 93 percent / conc. H2SO4 / 20 h / Heating 2: CH2Cl2 / 0.17 h / 5 °C 3: 97 percent / t-BuOK / 2 h / Heating 4: 96 percent / NBS / dimethylformamide / 4 h / 80 °C 5: 100 percent / aq. NaOH / methanol / 1.5 h / Heating View Scheme

1: 97 percent / t-BuOK / 2 h / Heating 2: 96 percent / NBS / dimethylformamide / 4 h / 80 °C 3: 100 percent / aq. NaOH / methanol / 1.5 h / Heating View Scheme

1: 60 percent / Et3N / dimethylformamide / 14 h / 20 °C 2: 100 percent / NBS / dimethylformamide / 2 h / 20 °C View Scheme

1: 100 percent / NBS / dimethylformamide / 2 h / 20 °C View Scheme

1.1: 96 percent / conc. H2SO4 / 6 h / Heating 2.1: t-BuOK / dimethylformamide / 0.25 h / 20 °C 2.2: dimethylformamide / 1 h / -30 °C 2.3: 87 percent / NaOMe / tetrahydrofuran / 2 h / Heating 3.1: 89 percent / 60 percent MCPBA / CH2Cl2 / 0.75 h / 20 °C 4.1: 90 percent / ethanol; dimethylformamide / 1 h / 60 °C 5.1: 96 percent / NBS / dimethylformamide / 4 h / 80 °C 6.1: 100 percent / aq. NaOH / methanol / 1.5 h / Heating View Scheme

1.1: t-BuOK / dimethylformamide / 0.25 h / 20 °C 1.2: dimethylformamide / 1 h / -30 °C 1.3: 87 percent / NaOMe / tetrahydrofuran / 2 h / Heating 2.1: 89 percent / 60 percent MCPBA / CH2Cl2 / 0.75 h / 20 °C 3.1: 90 percent / ethanol; dimethylformamide / 1 h / 60 °C 4.1: 96 percent / NBS / dimethylformamide / 4 h / 80 °C 5.1: 100 percent / aq. NaOH / methanol / 1.5 h / Heating View Scheme

Multistep reaction;