반응 #548161

반응 방정식

iodine

2,4-dimethyl-3-hydroxymethylthiophene

→

2,4-dimethyl-3-hydroxymethyl-5-iodothiophene

용매

benzene

반응 조건

후처리

1. 1
   기타was kept at room temperature
2. 2
   온도by cooling with an ice bath
3. 3
   workup.WAITwas continued for an additional hour
4. 4
   기타The mercuric iodide which precipitated
5. 5
   여과was filtered
6. 6
   세척washed well with warm ethyl ether
7. 7
   세척The combined organic solutions were washed with 10% sodium thiosulfate and saturated sodium chloride solution
8. 8
   기타dried
9. 9
   기타evaporated
10. 10
    workup.DISSOLUTIONThe resulting residue was dissolved in a minimum amount of hot ether
11. 11
    workup.ADDITIONan equal amount of hexane was added
12. 12
    기타The crystals which precipitated
13. 13
    여과were filtered
14. 14
    세척washed with cold hexane
15. 15
    기타to yield
16. 16
    건조after drying 2,4-dimethyl-3-hydroxymethyl-5-iodothiophene, m.p. 118.5°-120.5° C.

실험 절차

10.0 G. (46 mmol) of mercuric oxide and 14.7 g. (58 mmol) of iodine were added alternately over a period of 1 1/4 hrs. to a vigorously stirred solution of 8.2 g. (57.7 mmol) of 2,4-dimethyl-3-hydroxymethylthiophene in 300 ml. of benzene. The reaction mixture was kept at room temperature by cooling with an ice bath and stirring was continued for an additional hour. The mercuric iodide which precipitated was filtered and washed well with warm ethyl ether. The combined organic solutions were washed with 10% sodium thiosulfate and saturated sodium chloride solution, dried and evaporated. The resulting residue was dissolved in a minimum amount of hot ether, an equal amount of hexane was added and the solution cooled to -50° C. The crystals which precipitated were filtered and washed with cold hexane to yield after drying 2,4-dimethyl-3-hydroxymethyl-5-iodothiophene, m.p. 118.5°-120.5° C.

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