Bromine → 4-Bromo-5-methylthiophene-2-carbaldehyde

To a solution of 5-methylthiophene-2-carbaldehyde (2.00 g) in acetic acid (20 mL) was added dropwise bromine (0.90 mL). The reaction mixture was stirred at room temperature for 8 hr, saturated aqueous sodium hydrogen carbonate was added by small portions, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed successively with saturated aqueous sodium hydrogen carbonate, saturated sodium thiosulfate aqueous solution, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate) to give the title compound (2.11 g).

1. extractionthe mixture was extracted with ethyl acetate
2. washThe ethyl acetate layer was washed successively with saturated aqueous sodium hydrogen carbonate, saturated sodium thiosulfate aqueous solution
3. dry with materialdried over magnesium sulfate
4. concentrationconcentrated under reduced pressure
5. customThe residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate)

ORD record

ord-65de90b2c1544e299c31ee3b2e5d1bc7

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08461348B2