Hydrochloric Acid → HCID 21518587, compound

Under a nitrogen atmosphere, to a solution of 5-chloro-2-nitrobenzaldehyde (6.0 g, 32 mmol) in methylene chloride (40 mL), diethylaminosulfur trifluoride (5.0 mL, 38 mmol) was gradually added under ice-cooling, and the mixture was stirred at the same temperature for 1 hour. Saturated brine was added to stop the reaction, and after the precipitated solid was filtered, the mother liquid was extracted with methylene chloride. After it was dried with sodium sulfate, the solvent was distilled off under reduced pressure to give 4-chloro-2-(difluoromethyl)-1-nitrobenzene (6.0 g) as a crude product. The present compound was used for the subsequent reaction without further purification. Under a nitrogen atmosphere, to a solution of the above 4-chloro-2-(difluoromethyl)-1-nitrobenzene (6.0 g) in ethanol (0.10 L), stannous chloride dihydrate (28 g, 0.13 mol) and concentrated hydrochloric acid (20 mL) were successively added under ice-cooling, and the mixture was stirred at room temperature for 40 minutes. After the reaction, ethanol was distilled off under reduced pressure and a 5M aqueous sodium hydroxide solution was added under ice-cooling to make it basic. Thereafter, it was extracted with ethyl acetate and after it was successively washed with water and saturated brine, it was dried with sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane, 1:3, v/v) to give the title compound (4.2 g, 76%) as a solid.

1. customThe present compound was used for the subsequent reaction without further purification
2. temperaturecooling
3. distillationwas distilled off under reduced pressure
4. additiona 5M aqueous sodium hydroxide solution was added under ice-
5. temperaturecooling
6. extractionThereafter, it was extracted with ethyl acetate
7. washafter it was successively washed with water and saturated brine, it
8. dry with materialwas dried with sodium sulfate
9. distillationthe solvent was distilled off under reduced pressure
10. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane, 1:3

ORD record

ord-5a261b5e622a4b8abb3416501a23fb7e

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08642640B2