hydrogenchloride in acetone 1 h;

1: 1M NaOH / dioxane / 3 h 2: DCC / CH2Cl2 / 1 h / 0 °C 3: 87 percent / HBr / acetic acid / 0.5 h 4: 92 percent / Et3N / CH2Cl2 / 18 h 5: 65 percent / NaH / dimethylformamide / 1 h / 0 °C 6: 46 percent / 1M hydrochloric acid / acetone / 1 h View Scheme

1: 65 percent / NaH / dimethylformamide / 1 h / 0 °C 2: 46 percent / 1M hydrochloric acid / acetone / 1 h View Scheme

1: 87 percent / HBr / acetic acid / 0.5 h 2: 92 percent / Et3N / CH2Cl2 / 18 h 3: 65 percent / NaH / dimethylformamide / 1 h / 0 °C 4: 46 percent / 1M hydrochloric acid / acetone / 1 h View Scheme

1: DCC / CH2Cl2 / 1 h / 0 °C 2: 87 percent / HBr / acetic acid / 0.5 h 3: 92 percent / Et3N / CH2Cl2 / 18 h 4: 65 percent / NaH / dimethylformamide / 1 h / 0 °C 5: 46 percent / 1M hydrochloric acid / acetone / 1 h View Scheme

1: 92 percent / Et3N / CH2Cl2 / 18 h 2: 65 percent / NaH / dimethylformamide / 1 h / 0 °C 3: 46 percent / 1M hydrochloric acid / acetone / 1 h View Scheme