Bromine → 3-Bromo-2-methyl-1-benzothiophene

To a solution (50 mL) of 2-methyl-1-benzothiophene (5.00 g) in acetic acid was added dropwise bromine (1.90 mL) at 0° C., and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1, volume ratio) to give the title object compound (8.02 g, quantitative) as a brown oil.

1. concentrationThe reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution
2. additionwas added to the residue
3. extractionthe mixture was extracted with ethyl acetate
4. washThe extract was washed with saturated brine
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1, volume ratio)
8. customto give the title object compound (8.02 g, quantitative) as a brown oil

ORD record

ord-17d23703514a4608a82e75e6d660f236

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436043B2