Acetonitrile → 6-Bromo-benzo[b]thiophene-2-carboxylic acid methyl ester

Temperature

85 °C

TEA (1.29 g, 12.85 mmol) and mercapto-acetic acid methyl ester (1.14 g, 10.83 mmol) were added to acetonitrile (50 mL) previously purged with argon (10 minute). This was followed by the addition of 4-bromo-2-fluoro-benzaldehyde (2 g, 9.852 mmol) and the resulting mixture was heated to reflux at 85° C. overnight. The reaction was monitored by TLC (20% ethyl acetate in hexane). The reaction mixture was cooled, concentrated, basified with 10% NaOH solution and extracted with ethyl acetate to afford the crude product. Purification by column chromatography on silica gel (5% ethyl acetate in hexane) afforded 2.4 g of the product (90% yield).

1. custompreviously purged with argon (10 minute)
2. temperaturethe resulting mixture was heated
3. temperatureThe reaction mixture was cooled
4. concentrationconcentrated
5. extractionextracted with ethyl acetate
6. customto afford the crude product
7. customPurification by column chromatography on silica gel (5% ethyl acetate in hexane)

ORD record

ord-186542ce22ab474899cd0b1ec79ee476

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09029399B2