反应 #1836
ord-c9728215e0934ce58de5aa5e0e1a5863
反应方程式
反应条件
后处理
- 1其他A 1 L 3-neck round bottom flask equipped with a magnetic stirrer
- 2浓缩it was concentrated under vacuum to an oily residue that
- 3其他was partitioned between 100 mL of 1N aqueous sodium hydroxide and 100 mL of ether
- 4其他The aqueous layer was removed
- 5萃取extracted several times with ethyl acetate
- 6洗涤The combined extracts were washed with saturated aqueous sodium chloride
- 7干燥dried over magnesium sulfate
- 8过滤filtered
- 9浓缩concentrated under vacuum
- 10其他to give a white foam that
- 11其他was triturated with 100 mL of hot toluene
- 12温度The mixture was cooled in an ice bath
- 13其他the solids removed by filtration
- 14洗涤then washed with cold toluene, air
- 15其他dried
- 16其他dried under vacuum
实验过程
A 1 L 3-neck round bottom flask equipped with a magnetic stirrer, thermometer, dropping funnel and nitrogen bubbler was charged with 12.97 g (46.9 mmol) of 2-[2-(1H-tetrazol-5-yl)phenyl]-5-methylbenzofuran and 500 mL of 1,4-dioxane. To the well-stirred solution at room temperature was added a solution of 4.8 mL (93.2 mmol) of bromine in 35 mL of carbon tetrachloride dropwise over 1 hour. Cyclohexene (16 mL) was added to the reaction mixture then it was concentrated under vacuum to an oily residue that was partitioned between 100 mL of 1N aqueous sodium hydroxide and 100 mL of ether. The aqueous layer was removed, acidified with 50 mL of 2N aqueous hydrochloric acid, and extracted several times with ethyl acetate. The combined extracts were washed with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered and concentrated under vacuum to give a white foam that was triturated with 100 mL of hot toluene. The mixture was cooled in an ice bath and the solids removed by filtration then washed with cold toluene, air dried and dried under vacuum to give 14.11 g (39.7 mmol, 85%) of product. 1H NMR (200 MHz,CDCl3 +1 drop DMSO-d6): 2.44 (s,3H), 7.1-7.3 (m,4H), 7.6 (m,2H), 7.86 (m,1H), 7.95 (m,1H).