反応 #1833247

反応方程式

N,N-dimethylformamide

4-bromo-5-fluorobenzene-1,2-diol

cesium carbonate

bromochloromethane

→

5-bromo-6-fluorobenzo[d][1,3]dioxole

収率 85.0%

溶媒

Et2O

反応条件

後処理

1. 1
   温度was then heated to an external temperature of 80° C. for 3 h
2. 2
   温度Upon cooling
3. 3
   洗浄washed with water (50 mL)
4. 4
   洗浄a wash with saturated NaCl solution (50 mL)
5. 5
   乾燥The organic layer was dried over MgSO4
6. 6
   ろ過filtered

実験手順

To N,N-dimethylformamide (25 mL) in a 50 mL flask was added 4-bromo-5-fluorobenzene-1,2-diol (2 g, 9.66 mmol), cesium carbonate (4.72 g, 14.49 mmol) and bromochloromethane (1.875 g, 14.49 mmol). The reaction mixture was allowed to stir at room temperature for 1 h and was then heated to an external temperature of 80° C. for 3 h. Upon cooling, the reaction mixture was diluted with Et2O (75 mL) and washed with water (50 mL) followed by a wash with saturated NaCl solution (50 mL). The organic layer was dried over MgSO4 and filtered. Concentration of the organic solution gave 5-bromo-6-fluorobenzo[d][1,3]dioxole as a light orange solid (1.8 g, 85%): 1H NMR (400 MHz, CDCl3) δ 6.94 (d, J=5.9 Hz, 1H), 6.67 (d, J=7.9 Hz, 1H), 6.00 (s, 2H); 19F NMR (376 MHz, CDCl3) δ −113.82 (s); ESIMS m/z 220 ([M+H]+), 218 ([M−H]−).

出典