반응 #1836
ord-c9728215e0934ce58de5aa5e0e1a5863
반응 방정식
반응 조건
후처리
- 1기타A 1 L 3-neck round bottom flask equipped with a magnetic stirrer
- 2농축it was concentrated under vacuum to an oily residue that
- 3기타was partitioned between 100 mL of 1N aqueous sodium hydroxide and 100 mL of ether
- 4기타The aqueous layer was removed
- 5추출extracted several times with ethyl acetate
- 6세척The combined extracts were washed with saturated aqueous sodium chloride
- 7건조dried over magnesium sulfate
- 8여과filtered
- 9농축concentrated under vacuum
- 10기타to give a white foam that
- 11기타was triturated with 100 mL of hot toluene
- 12온도The mixture was cooled in an ice bath
- 13기타the solids removed by filtration
- 14세척then washed with cold toluene, air
- 15기타dried
- 16기타dried under vacuum
실험 절차
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).