반응 #1532

반응 방정식

ammonium chloride

n-butyl lithium

N-t-butyl-3-bromo-2-thiophenesulfonamide

ethyl fluoroacetate

→

pure title compound

수율 72.0%

N-t-butyl-3-(fluoroacetyl)-2-thiophenesulfonamide

수율 72.0%

용매

ethylacetate

tetrahydrofuran

반응 조건

후처리

1. 1
   온도the temperature of the mixture was raised slowly to -20° C.
2. 2
   온도again cooled to -78° C
3. 3
   온도The temperature of the mixture was raised again slowly to -20° C.
4. 4
   기타to separate the organic layer
5. 5
   건조The extracted organic layer was dried over anhydrous magnesium sulfate
6. 6
   농축concentrated

실험 절차

2.98 g (0.0mole) of N-t-butyl-3-bromo-2-thiophenesulfonamide was dissolved in 50mi of dry tetrahydrofuran and the mixture was cooled to -78° C. under nitrogen gas. To the reaction solution was slowly added dropwise 8.4 ml of n-butyl lithium (2.5N) and then the temperature of the mixture was raised slowly to -20° C. and again cooled to -78° C. 1.2 g (0.011 mole) of ethyl fluoroacetate was added slowly to the reaction mixture. The temperature of the mixture was raised again slowly to -20° C. and then the mixture was stirred for 10 minutes. To the reaction mixture was added 100 ml of 5% aqueous ammonium chloride solution, and then added 100 ml of ethylacetate to separate the organic layer. The extracted organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was subjeced to column chromatography on silica gel to obtain 2.0 g (Yield: 72%) of the pure title compound as a liquid.

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