Dimethylformamide → 3-Fluoro-2-formyl-N,N-diisopropyl-5-trifluoromethyl-benzamide

Temperature

-75 °C

A dried 200 ml round-bottomed flask containing 20 ml diethylether was cooled to −75° C. then 22.15 mmol diisopropylamine, 22.15 mmol 1.6M n-butyllithium in hexane, and a solution of 14.77 mmol 3-fluoro-N,N-diisopropyl-5-trifluoromethyl-benzamide in 20 ml diethylether were added sequentially. The mixture was stirred at −75° C. for 2 hours. 2.9 ml DMF was added dropwise. After the reaction was stirred for another hour, the mixture was warmed and stirred at room temperature for 30 minutes. The mixture was quenched with 100 ml 10% citric acid and extracted 3 times with ether. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography (SiO2, heptane/ethyl acetate) to yield the title compound as a light yellow solid (90% yield). MS (m/e): 320.1 (M+H+, 100%)

1. stirringAfter the reaction was stirred for another hour
2. temperaturethe mixture was warmed
3. stirringstirred at room temperature for 30 minutes
4. customThe mixture was quenched with 100 ml 10% citric acid
5. extractionextracted 3 times with ether
6. dry with materialThe combined organic phases were dried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe residue was purified by chromatography (SiO2, heptane/ethyl acetate)

ORD record

ord-d9950938bc1a496fa698b27d2dc3cac0

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188139B2