Structure of 123572-63-4
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CAS No. : | 123572-63-4 |
Formula : | C7H5F4NO |
M.W : | 195.11 |
SMILES Code : | NC1=CC(F)=CC=C1OC(F)(F)F |
MDL No. : | MFCD16652514 |
Boiling Point : | No data available |
InChI Key : | AUJAYNLPYRARLU-UHFFFAOYSA-N |
Pubchem ID : | 14439307 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H312-H315-H319-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338-P304+P340-P405-P501 |
* 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 triethylamine; In dichloromethane; for 16h; | Without purification, the phenylamines (7 g, 35.8 mmol) were suspended in dichloromethane (100mL), treated with trifluoroacetic anhydride (71 mmol) and triethylamine (20 mL) for 16h. The reaction mixture was washed with saturated NaHCO3 and brine. The organic phase was further purified by silica gel chromatography (hexane/EtOAc 9:1) to give a mixture (5.29g) of 2,2,2-trifluoro-N-(5-fluoro-2-trifluoromethoxy-phenyl)-acetamide and its isomer in 1:4 ratio, which was nitrated in a same procedure as the first step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; hydrogen;palladium 10% on activated carbon; In ethanol; under 2585.81 Torr; for 3.5h; | The crude nitration product (6.05 g) was dissolved in ethanol (40 mL) and shacked with 10% Pd/C (310 mg) and concentrate HCl (2.8 mL) under H2 (50 psi) for 3.5 h. Filtration and concentration gave a mixture (8.0g) of 5-fluoro-2-trifluoromethoxy-phenylamine and its isomer 2-fluoro-5-trifluoromethoxy-phenylamine in 3:1 ratio. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A. 1 -Fluoro-2-nitro-4-trifluoromethoxy-benzene and 4-Fluoro-2-nitro-1 - trifluoromethoxy-benzeneTo a mixture of 1-fluoro-4-trifluoromethoxy-benzene (31.57 g, 0.18 mol) in cone. H2SO4 (100 ml_) at 0C is added cone. HNO3 (30 ml_) dropwise over a 10 min period. After the mixture is stirred at 0 C for 1 h, it was poured into ice. The mixture is extracted with EtOAc. The organic extract is washed with H2O (3x) and brine, dried over MgSO4, filtered, and concentrated in vacuo to yield 38 g (96%) of the product as a mixture of 1 -fluoro-2-nitro-4-trifluoromethoxy-benzene and 4-fluoro-2-nitro-1 - trifluoromethoxy-benzene (-30/70, based upon 19F NMR). 1H NMR (CDCI3): δ 8.00- 7.90 and 7.80-7.65 (m, 1 H), 7.60-7.25 (m, 2H); 19 F NMR (CDCI3) δ -57.59 and -58.11 (s, 3F), -109.07 and -117.90 (t, J = 6.2 and d, J = 6.2, 1 F).B. 2-Fluoro-5-trifluoromethoxy-phenylamine and 5-Fluoro-2-trifluoromethoxy- phenvlamine A mixture of 1 -fluoro-2-nitro-4-trifluoromethoxy-benzene and 4-fluoro-2-nitro-1 - trifluoromethoxy-benzene and Raney Ni (2800) in MeOH (250 ml_) is hydrogenated at 40 psi for 5 h (or until no more H2 is consumed). The catalyst is filtered off, and the filtrate is concentrated in vacuo. The residue is redissolved in CH2CI2, dried over MgSO4, filtered, and concentrated in vacuo to yield 27.4 g of the product (dark brown liquid) as a mixture of 2-fluoro-5-trifluoromethoxy-phenylamine and 5-fluoro-2- trifluoromethoxy-phenylamine (-30/70, based upon 19F NMR). 1H NMR (CDCI3): δ 7.15-6.90 (m, 1 H), 6.70-6.30 (m, 2H), 3.60-4.25 (br m, 1 H); 19 F NMR (CDCI3) δ -57.77 and -57.86 (s, 3F), -113.83 and -137.09 (1 H); MS 196 (M+1 , 100%). |
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