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CAS No. : | 114973-22-7 | MDL No. : | MFCD00190121 |
Formula : | C7H4F5N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FPEXXFHBKBTGJL-UHFFFAOYSA-N |
M.W : | 197.11 | Pubchem ID : | 2737647 |
Synonyms : |
|
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P261-P280-P305+P351+P338-P311 | UN#: | 2810 |
Hazard Statements: | H302+H312-H315-H319-H331-H335 | Packing Group: | Ⅲ |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; In dichloromethane; | STR44 With stirring, 11.7 g (104 mmol) of ethyl chloroformate are added to a mixture of 20.5 g (104 mmol) of <strong>[114973-22-7]2,5-difluoro-4-trifluoromethyl-aniline</strong>, 8.5 g of pyridine and 200 ml of dichloromethane which had been cooled to 0 C. The reaction mixture is stirred at 0 C. for 60 minutes and then washed with 2N hydrochloric acid and with water, dried with sodium sulphate and filtered. The filtrate is concentrated under water pump vacuum, the residue is digested with petroleum ether and the crystalline product is isolated by filtration with suction. This gives 26.2 g (93.5% of theory) of N-(2,5-difluoro-4-trifluoromethyl-phenyl)-O-ethyl-urethane of melting point 92 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In hexane; toluene; | Production example 3 [Production of the present compound (3)] 0.20 Gram of 2,5-difluoro-4-trifluoromethylaniline was dissolved in 4 ml of toluene, and to this solution, a solution of 0.20 g of 2,4,6-trifluorobenzoylisocyanate in 2 ml of toluene was added dropwise with stirring and ice-cooling. After completion of the addition, stirring was continued overnight at room temperature and then 5 ml of hexane was added. The precipitated crystals were collected by filtration and dried to give 0.31 g of N-2,4,6-trifluorobenzoyl-N'-2,5-difluoro-4-trifluoromethylphenylurea as white crystals. m.p. 171.6C Yield 78% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With sulfuric acid; In methanol; | Production example 2 1.35 Grams of 2,5-difluoro-4-trifluoromethylacetanilide was added to a mixed solvent of 10 ml of 20% sulfuric acid and 10 ml of methanol, followed by stirring under reflux at 80C for 2 hours. The reaction mixture was then cooled and extracted with 50 ml of dichloromethane, and the dichloromethane layer was washed with water and dried over anhydrous sodium sulfate. After removing dichloromethane by evaporation under reduced pressure, the residue obtained was distilled to obtain 1.10 g of 2,5-difluoro-4-trifluoromethylaniline. Yield 99% b.p. 170- 172C/15 mmHg 1H-NMR (solvent, deutero chloroform; internal standard, TMS) δ(ppm) 3.80-4.70 (br., 2H), 6.52 (dd, 1H, J=8.0 Hz, 11.0 Hz), 7.16 (dd, 1H, J=7.5 Hz, 12.0 Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 45.0℃; for 3.0h; | A slightly yellow solution of 2,5-difluoro-4-(trifluoromethyl)aniline (10.0 ml; 76.708 mmol) in MeCN (90 ml) was treated with copper(ll) bromide (17.133 g; 76.708 mmol), and the green heterogeneous mixture was heated to 45C. A solution of tert-butyl nitrite (10.0 ml; 84.379 mmol) in MeCN (20 ml) was then added dropwise over 30 min., and the resulting mixture was further stirred at 45C for 2h30. The dark-green heterogeneous reaction mixture was allowed to cool to rt, and was directly purified by FC (DCM). After concentration to dryness under reduced pressure, the expected product 1-bromo-2,5-difluoro-4-trifluoromethyl- benzene was obtained as an orange oil (10.290 g; 51 %). LC-MS: tR = 1.07 min.; [M+H]+: no ionisation. |
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