Iodine → Dibutyl[4-[2-(thiophene-2-yl)vinyl]phenyl]amine

In a stream of argon, to 70 ml of tetrahydrofuran was added 10.45 g of phenyllithium (19% solution in dibutylether) (23.6 mmol), and 8.09 g (20.5 mmol) of 2-thenyl triphenylphosphonium chloride was added thereto under cooling. To this mixture was added dropwise 4.92 g (21.0 mmol) of 4-(dibutylamino)benzaldehyde. The mixture was stirred at the same temperature for 1 hour. After the reaction mixture was poured into water, extraction with toluene, washing with a saturated saline solution, drying over anhydrous sodium sulfate, and concentration were performed. The residue was purified by silica gel column chromatography to give an orange liquid. This liquid was dissolved in 200 ml of toluene and 200 mg of iodine was added thereto. After stirred at room temperature for 15 minutes, the mixture was added to water and the phases were separated. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography to give 6.09 g of an orange oily matter (yield: 94.8%).

1. additionwas added
2. temperatureunder cooling
3. washwashing with a saturated saline solution
4. dry with materialdrying over anhydrous sodium sulfate, and concentration
5. customThe residue was purified by silica gel column chromatography
6. customto give an orange liquid
7. stirringAfter stirred at room temperature for 15 minutes
8. customthe phases were separated
9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
10. concentrationconcentrated
11. customThe residue was purified by silica gel column chromatography
12. customto give 6.09 g of an orange oily matter (yield: 94.8%)

ORD record

ord-410f12d1564b41fabda73dba90ee31bb

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846955B2