Hydrochloric Acid → 3,4,5-Trifluorobenzaldehyde

Temperature

40 °C

In a nitrogen atmosphere, a solution prepared by dissolving 50 g of 3,4,5-trifluorobromobenzene in 50 mL of THF was added dropwise at a rate that caused gentle reflux to a mixed solution of 6.34 g of magnesium and 60 mL of THF. After dropwise addition, the mixture was stirred at 40° C. for 1 hour. Then, a solution prepared by dissolving 34.64 g of DMF in 60 mL of THF was added dropwise under ice cooling at such a rate that the inside temperature did not exceed 20° C., followed by stirring at room temperature for 1 hour. Then, 10% hydrochloric acid was added until the reaction system became acidic, and the mixture was stirred at room temperature for 1 hour. Then, hexane was added to the mixture to separate an organic layer, and an aqueous layer was subjected to extraction with hexane. The hexane extract was combined with the organic layer and washed with a saturated aqueous sodium bicarbonate solution and saturated brine. The resultant mixture was dried by adding sodium sulfate, and then the solvent was distilled off under reduced pressure to yield 37.91 g of 3,4,5-trifluorobenzaldehyde.

1. customIn a nitrogen atmosphere, a solution prepared
2. additionwas added dropwise at a rate that
3. additionAfter dropwise addition
4. customThen, a solution prepared
5. additionwas added dropwise under ice cooling at such a rate that the inside temperature
6. customdid not exceed 20° C.
7. stirringby stirring at room temperature for 1 hour
8. stirringthe mixture was stirred at room temperature for 1 hour
9. customto separate an organic layer
10. extractionan aqueous layer was subjected to extraction with hexane
11. extractionThe hexane extract
12. washwashed with a saturated aqueous sodium bicarbonate solution and saturated brine
13. dry with materialThe resultant mixture was dried
14. additionby adding sodium sulfate
15. distillationthe solvent was distilled off under reduced pressure

ORD record

ord-1e1581e1464e4985b48e5739af3d62b3

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916718B2