N-bromobutanimide → Methyl 5-bromo-2-methylfuran-3-carboxylate

Temperature

0 °C

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.

1. additionUpon completion of the addition
2. customthe ice-water bath was removed
3. filtrationThe mixture was filtered
4. concentrationthe filtrate was concentrated under reduced pressure
5. customThe residue was purified by silica gel column chromatography

ORD record

ord-cc09c0e355394ac299b72b7d79f62f71

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367710B2