Hydrochloric Acid → Methyl 5-bromo-3-formylthiophene-2-carboxylate

Temperature

80 °C

Silver nitrate (1.43 g, 8.39 mmol) was added to a mixed solution of methyl 5-bromo-3-(dibromomethyl)thiophene-2-carboxylate obtained in Example (246a) (1.57 g, 4.00 mmol) in ethanol/water (30 mL/10 mL), and the mixture was stirred at 80° C. for three hours. Concentrated hydrochloric acid was added to the reaction solution at 0° C., and then the mixture was filtered. The filtrate was concentrated under reduced pressure. Then, saturated aqueous sodium bicarbonate solution was added to the resulting residue, and the aqueous layer was extracted with chloroform. The combined organic layers were dried over anhydrous magnesium sulfate, and then the filtrate was concentrated under reduced pressure to obtain 980 mg of the title compound as a pale yellow solid (98%).

1. filtrationthe mixture was filtered
2. concentrationThe filtrate was concentrated under reduced pressure
3. additionThen, saturated aqueous sodium bicarbonate solution was added to the resulting residue
4. extractionthe aqueous layer was extracted with chloroform
5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
6. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-21dd73de0b3748d09e3ba0c22c6cead1

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08927588B2