반응 #471582

반응 방정식

2-Methyl-furan-3-carboxylic acid methyl ester

N-bromosuccinimide

→

5-bromo-2-methyl-furan-3-carboxylic acid methyl ester

수율 61.0%

용매

toluene

반응 조건

후처리

1. 1
   workup.ADDITIONUpon completion of the addition
2. 2
   기타the ice-water bath was removed
3. 3
   여과The mixture was filtered
4. 4
   농축the filtrate was concentrated under reduced pressure
5. 5
   기타The residue was purified by silica gel column chromatography

실험 절차

2-Methyl-furan-3-carboxylic acid methyl ester (2.0 g, 14.3 mmol) was dissolved in toluene followed by addition of 2,2′-azobis(2-methylpropionitrile) (10 mg, 0.06 mmol). The mixture was cooled to 0° C. by an ice-water bath followed by addition of N-bromosuccinimide (2.8 g, 15.7 mmol). Upon completion of the addition, the ice-water bath was removed and the reaction mixture was stirred at room temperature overnight. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound 5-bromo-2-methyl-furan-3-carboxylic acid methyl ester 53a (1.9 g, yield 61%) as a colourless oil.

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