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

To a solution of 2-bromo-3-methylthiophene (2.66 g, 15.0 mmol) in dry THF (10 mL) at −65° C. was added LDA solution (15.0 mmol) dropwise. After stirring for 30 min, DMF (3.0 g, 10.0 mmol) in dry THF (3 mL) was added dropwise and the reaction was stirred at −65° C. for 2 h. The reaction was warmed to room temperature and water was added. The quenched mixture was extracted with EtOAc (3×100 mL). The combined extract was washed with brine and dried over anhydrous Na2SO4. After filtration and concentration, the crude product was purified by column chromatography to give the title compound.

1. stirringthe reaction was stirred at −65° C. for 2 h
2. extractionThe quenched mixture was extracted with EtOAc (3×100 mL)
3. extractionThe combined extract
4. washwas washed with brine
5. dry with materialdried over anhydrous Na2SO4
6. filtrationAfter filtration and concentration
7. customthe crude product was purified by column chromatography

ORD record

ord-a2fc707664ac4e51a3b1318adf61823d

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08710245B2