Acetaldehyde → HCID 68408178, compound

Temperature

-20 °C

At −78° C. under nitrogen 1.8 M phenyl magnesium chloride solution in THF (3.06 ml, 5.5 mmol) were added dropwise to 2,6-dibromo-4-chloroaniline (1.426 g, 5.0 mmol) in THF (25 ml). The clear solution was warmed to −20° C. and stirred at this temperature for 5 minutes. The clear yellow solution was cooled to −78° C. and 1.6 M n-butyllithium solution in hexane (6.25 ml, 10 mmol) was added dropwise. The reaction was warmed to −10° C. and again cooled to −78° C. at which temperature acetaldehyde (440 mg, 10 mmol) dissolved in THF (5 ml) was added. After stirring for 10 minutes at −78° C. 1N aqueous hydrogen chloride solution was added and the reaction was allowed to warm to room temperature. The reaction was extracted twice with diethyl ether, dried over sodium sulfate, filtered and the solvent was evaporated to yield the product as a mixture of the corresponding amine, imine and aminal. The crude product was used directly in the next step.

1. temperatureThe clear yellow solution was cooled to −78° C.
2. temperatureThe reaction was warmed to −10° C.
3. additionwas added
4. stirringAfter stirring for 10 minutes at −78° C
5. temperatureto warm to room temperature
6. extractionThe reaction was extracted twice with diethyl ether
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. customthe solvent was evaporated
10. customto yield the product

ORD record

ord-4be1bf62baf94a56b778100f86d5cfed

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07781441B2