4-Chlorobenzaldehyde → HCID 68293607, compound

Temperature

-78 °C

An oven-dried round-bottomed flask was charged with 4,5-diiodothiophene-2-carbonitrile (1.80 g, 5.0 mmol). After degassed, anhydrous THF (15 mL) was added through syringe. After cooled to −78° C., i-PrMgCl (3 mL, 2.0 M, 6.0 mmol) was added dropwise. The reaction was further stirred for 30 min at −78° C. after complete addition. 4-chlorobenzaldehyde (0.98 g, 7.0 mmol) in 5 mL THF was then added. After stirring for 10 min at −78° C. for 1 h, the reaction mixture was warmed to room temperature. 50 mL of saturated aqueous NH4Cl was added. The reaction mixture was extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulphate and then concentrated. The residue was purified by flash chromatography (hexane:EtOAc:CH2CL2=30:3:10). 1.39 g (74%) of product was obtained as a white solid.

1. customAfter degassed
2. additionanhydrous THF (15 mL) was added through syringe
3. additionafter complete addition
4. stirringAfter stirring for 10 min at −78° C. for 1 h
5. temperaturethe reaction mixture was warmed to room temperature
6. extractionThe reaction mixture was extracted with ethyl acetate
7. dry with materialThe organic phase was dried over anhydrous sodium sulphate
8. concentrationconcentrated
9. customThe residue was purified by flash chromatography (hexane:EtOAc:CH2CL2=30:3:10)

ORD record

ord-0e2f2f88f7c84182819754c4f1e7c8e5

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09012655B2