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

To a solution of 5-methylthiophene-2-carbaldehyde (50.0 g) in acetic acid (400 mL) was added dropwise a solution of bromine (25 mL) in acetic acid (200 mL) at room temperature over 6 hr. After the dropwise addition, the reaction mixture was stirred overnight, neutralized with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was dissolved in toluene (50 mL), and the mixture was stirred at 110° C. for 2 hr and concentrated. The residue was subjected to silica gel column chromatography, eluted with ethyl acetate-hexane (1:5, volume ratio) and concentrated to give 4-bromo-5-methylthiophene-2-carbaldehyde (40.0 g, yield 50%) as yellow crystals. melting point 60° C.

1. additionAfter the dropwise addition
2. extractionextracted with ethyl acetate
3. washThe ethyl acetate layer was washed with saturated brine
4. dry with materialdried (MgSO4)
5. concentrationconcentrated
6. dissolutionThe obtained residue was dissolved in toluene (50 mL)
7. stirringthe mixture was stirred at 110° C. for 2 hr
8. concentrationconcentrated
9. washeluted with ethyl acetate-hexane (1:5, volume ratio)
10. concentrationconcentrated

ORD record

ord-a5c4e52c31994f848de269f47521ebcb

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08492405B2