반응 #1447105

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N-Iodosuccinimide

3-bromo-2-methyl-benzoic acid

→

3-Bromo-5-iodo-2-methyl-benzoic acid

용매

sulphuric acid

sulphuric acid

반응 조건

후처리

1. 1
   workup.ADDITIONis added at such a rate that the solution temperature
2. 2
   온도maintained below 5° C
3. 3
   온도before warming to room temperature over night
4. 4
   workup.ADDITIONThen, the mixture is poured
5. 5
   추출the resultant solution is extracted with ethyl acetate
6. 6
   세척The combined extracts are washed in succession with aqueous 10% Na2S2O3 solution (2×), water (3×), and brine (1×)
7. 7
   건조After drying (MgSO4) the organic layer
8. 8
   기타the solvent is evaporated under reduced pressure
9. 9
   기타to give a solid
10. 10
    기타The solid is triturated with 70° C.-
11. 11
    온도warm water
12. 12
    기타separated from the water by filtration
13. 13
    기타dried
14. 14
    기타After the solid is triturated with little ether
15. 15
    여과filtered
16. 16
    기타dried
17. 17
    기타the product is obtained as a white solid

실험 절차

N-Iodosuccinimide (5.8 g) is added in portions to an ice-cold solution of sulphuric acid (20 mL). The resulting mixture is stirred for 40 min before 3-bromo-2-methyl-benzoic acid (5.0 g) dissolved in sulphuric acid (20 mL) is added at such a rate that the solution temperature maintained below 5° C. The mixture is stirred at 5-10° C. for another 3 h before warming to room temperature over night. Then, the mixture is poured on crushed ice (300 g) and the resultant solution is extracted with ethyl acetate. The combined extracts are washed in succession with aqueous 10% Na2S2O3 solution (2×), water (3×), and brine (1×). After drying (MgSO4) the organic layer, the solvent is evaporated under reduced pressure to give a solid. The solid is triturated with 70° C.-warm water, separated from the water by filtration and dried. After the solid is triturated with little ether, filtered and dried, the product is obtained as a white solid.

출처