Methanol → Methyl 5-bromothiophene-2-carboxylate

Concentrated H2SO4 (3 mL) was added to a solution of 5-bromothiophene-2-carboxylic acid (5.0 g, 2.42 mmol) in methanol (100 mL). The reaction mixture was heated to reflux for 16 hours. After cooling to ambient temperature, the reaction mixture was concentrated to dryness. The residue was dissolved in EtOAc (60 mL), washed with saturated sodium carbonate (60 mL), and saturated sodium chloride (40 mL) and dried over anhydrous sodium sulfate. The solution was concentrated to give the compound 1021 (4.8 g). 1H NMR (CDCl3, 300 MHz) δ 3.90 (s, 3H), 7.09-7.10 (d, 1H), 7.57-7.58 (d, 1H).

1. temperatureThe reaction mixture was heated
2. temperatureto reflux for 16 hours
3. concentrationthe reaction mixture was concentrated to dryness
4. dissolutionThe residue was dissolved in EtOAc (60 mL)
5. washwashed with saturated sodium carbonate (60 mL), and saturated sodium chloride (40 mL)
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationThe solution was concentrated

ORD record

ord-757bcea8d97b4568941dc9996c76750d

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08507647B2