Dimethylformamide → 2,4,6-Trichlorobenzaldehyde

Temperature

-78 °C

2,4,6-Trichlorobenzaldehyde was prepared according to the procedure outlined in Synthesis 2008, 279. To a solution of 1,3,5-trichlorobenzene (10.0 g, 55.1 mmol) in THF (200 ml) at −78° C. was slowly added n-BuLi (1.6 M in hexanes, 34.4 ml, 55.1 mmol) over 20 min. The reaction mixture was stirred at −78° C. for 30 min then DMF (7.5 ml, 96.4 mmol) was added dropwise. The reaction was stirred at −78° C. for an additional 1.5 h then quenched with 3 N HCl (200 ml) and warmed to room temperature. The mixture was extracted with EtOAc. The organic layer was washed with sat NaHCO3 and brine then dried over MgSO4 and concentrated to afford 10.7 g (93%) of 2,4,6-trichlorobenzaldehyde as a white solid.

1. custom2,4,6-Trichlorobenzaldehyde was prepared
2. customoutlined in Synthesis 2008, 279
3. customat −78° C.
4. customover 20 min
5. stirringThe reaction was stirred at −78° C. for an additional 1.5 h
6. customthen quenched with 3 N HCl (200 ml)
7. temperaturewarmed to room temperature
8. extractionThe mixture was extracted with EtOAc
9. washThe organic layer was washed with sat NaHCO3 and brine
10. dry with materialthen dried over MgSO4
11. concentrationconcentrated

ORD record

ord-8b87152df51643b3b7bba595d664ef10

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08658646B2