تفاعل #1836

معادلة التفاعل

Cyclohexene

bromine

2-[2-(1H-tetrazol-5-yl)phenyl]-5-methylbenzofuran

1,4-dioxane

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product

المردود 85.0%

3-Bromo-2-[2-(1H-tetrazol-5-yl)phenyl]-5-methylbenzofuran

المردود 85.0%

المذيبات

carbon tetrachloride

ظروف التفاعل

المعالجة

1. 1
   أخرىA 1 L 3-neck round bottom flask equipped with a magnetic stirrer
2. 2
   تركيزit was concentrated under vacuum to an oily residue that
3. 3
   أخرىwas partitioned between 100 mL of 1N aqueous sodium hydroxide and 100 mL of ether
4. 4
   أخرىThe aqueous layer was removed
5. 5
   استخلاصextracted several times with ethyl acetate
6. 6
   غسيلThe combined extracts were washed with saturated aqueous sodium chloride
7. 7
   تجفيفdried over magnesium sulfate
8. 8
   ترشيحfiltered
9. 9
   تركيزconcentrated under vacuum
10. 10
    أخرىto give a white foam that
11. 11
    أخرىwas triturated with 100 mL of hot toluene
12. 12
    درجة الحرارةThe mixture was cooled in an ice bath
13. 13
    أخرىthe solids removed by filtration
14. 14
    غسيلthen washed with cold toluene, air
15. 15
    أخرىdried
16. 16
    أخرىdried under vacuum

الإجراء التجريبي

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).

المصدر