Dimethylformamide → 3,4-Dibromothiophene-2-carbaldehyde

Temperatur

-78 °C

To a solution of diisopropylamine (1.3 g, 12.5 mmol) in 15 mL of anhydrous THF was added n-BuLi (4.0 mL, 2.5 M in hexane) at −78° C. After the mixture was stirred at −78° C. for 0.5 h 3,4-dibromothiophene (2 g, 8.3 mmol) in anhydrous THF (20 mL) was added. The mixture was stirred at −78° C. for 15 min., a solution of DMF (670 mg, 9.2 mmol) in THF (5 mL) was added. After being stirred at this temperature for 0.5 h, the mixture was stirred at room temperature for 2 hours. The mixture was quenched with NH4Cl saturated solution, diluted with water, extracted with EtOAc, concentrated, and purified by column chromatography to give 3,4-dibromothiophene-2-carbaldehyde (1.0 g, yield 45%).

1. additionwas added
2. stirringAfter being stirred at this temperature for 0.5 h
3. stirringthe mixture was stirred at room temperature for 2 hours
4. customThe mixture was quenched with NH4Cl saturated solution
5. additiondiluted with water
6. extractionextracted with EtOAc
7. concentrationconcentrated
8. custompurified by column chromatography

ORD-Eintrag

ord-042df813076047b9b71c0afc7bc06f38

Quelldatensatz

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08859611B2