Dimethylformamide → N-(4-formyl-3,5-dimethyl-phenyl)-acetamide

Temperature

-78 °C

To a solution of N-(4-bromo-3,5-dimethyl-phenyl)-acetamide (150 mg) in THF (5 mL) was added n-BuLi (1.36 mL, 1.0 M solution in hexane) at −78° C. The mixture was stirred at −78° C. for 30 min, then warmed up to −40° C. for 5 min, then cooled down to at −78° C. again. After 20 min, DMF (0.24 mL) was added. The mixture was stirred at −78° C. for 30 min and then allowed to warm up to room temperature for 1 h. The reaction was quenched with saturated NH4Cl aqueous solution and extracted with EtOAc. The organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give N-(4-formyl-3,5-dimethyl-phenyl)-acetamide: MS (m/z) 192 (M+1).

1. temperaturewarmed up to −40° C. for 5 min
2. temperaturecooled down to at −78° C. again
3. waitAfter 20 min
4. stirringThe mixture was stirred at −78° C. for 30 min
5. temperatureto warm up to room temperature for 1 h
6. customThe reaction was quenched with saturated NH4Cl aqueous solution
7. extractionextracted with EtOAc
8. washThe organic extracts were washed with brine
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure

ORD record

ord-54ca4c150d3345b795c0bcc0dad7c55d

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08222248B2