반응 #2355149

반응 방정식

water

4-(4-methylphenyl)-1,2,3,5-(1H)-tetrazole

potassium carbonate

1-bromo-2-fluoroethane

→

1-(2-fluoroethyl)-(4-methylphenyl)-1,2,3,5-(1H)-tetrazole

수율 43.8%

용매

acetonitrile

반응 조건

후처리

1. 1
   온도to reflux
2. 2
   workup.ADDITIONUpon completion of the addition the reaction mixture
3. 3
   기타was placed in a water bath
4. 4
   온도cooled to 0° C.
5. 5
   온도After this time the reaction mixture was heated
6. 6
   온도to reflux
7. 7
   workup.STIRRINGwhere it stirred for three hours
8. 8
   온도cooled to 0° C.
9. 9
   workup.STIRRINGwhere it stirred for about 18 hours
10. 10
    추출The resulting solution was extracted with three 50 mL portions of ethyl acetate
11. 11
    농축The combined extracts were concentrated under reduced pressure to a residue, which
12. 12
    세척Elution
13. 13
    농축concentrated under reduced pressure

실험 절차

Under a nitrogen atmosphere, a stirred solution of 5.0 grams (0.031 mole) 4-(4-methylphenyl)-1,2,3,5-(1H)-tetrazole and 4.8 grams (0.035 mole) of potassium carbonate in 150 mL of acetonitrile was heated to reflux and then cooled to ambient temperature. To this was slowly added 10.0 grams (0.078 mole) of 1-bromo-2-fluoroethane. Upon completion of the addition the reaction mixture was placed in a water bath and cooled to 0° C., where it stirred for one hour. After this time the reaction mixture was heated to reflux, where it stirred for three hours, and then cooled to 0° C., where it stirred for about 18 hours. At the conclusion of this period the reaction mixture was poured into 50 mL of water. The resulting solution was extracted with three 50 mL portions of ethyl acetate. The combined extracts were concentrated under reduced pressure to a residue, which was subjected to column chromatography on silica gel. Elution was accomplished with methylene chloride and acetone. The product-containing fractions were combined and concentrated under reduced pressure, yielding 2.8 grams 1-(2-fluoroethyl)-(4-methylphenyl)-1,2,3,5-(1H)-tetrazole. The NMR spectrum was consistent with the proposed structure.

출처