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• W1874255178 abstract "[34025-21-3] C10H7F6NO (MW 271.16)InChI = 1S/C10H7F6NO/c1-18-7-4-2-6(3-5-7)17-8(9(11,12)13)10(14,15)16/h2-5H,1H3InChIKey = FRNUJUDPEZOYJD-UHFFFAOYSA-N(building block1 for trifluoromethylated N-heterocycles, amino acids, and peptides)Physical Data: slightly yellow colored liquid, bp 78–81 °C/28 Torr or 105–110 °C/50 Torr.Solubility: sol THF, CH2Cl2, EtOAc, Tol.Handling, Storage, and Precautions: store under nitrogen atmosphere in a refrigerator. Compound is moisture sensitive and is hydrated easily on exposure to moisture.Preparation: The title compound is prepared by the conventional acid-catalyzed condensation of hexafluoroacetone with p-anisidine in the presence of POCl3 (eq 1)2. (1)Typical preparation method: In a 3000 mL flask, a solution of p-anisidine (123 g, 1.0 mol) in 1500 mL dichloromethylene was cooled at about −40 °C, and then was bubbled into hexafluoroacetone gas that was generated by slowly dropping hexafluoroacetone trihydrate (265 g, 1.2 mol) into concentrated sulfuric acid (133 mL) at 90 °C over 8 h (apparatus for generation and reaction with p-anisidine of dry hexafluoroacetone is available in supporting information of Ref. 2). The moisture-sensitive adduct of hexafluoroacetone with p-anisidine gradually formed as a pale violet precipitate. Addition of triethylamine (415 mL, 3.0 mol) dissolved the precipitate. The flask was equipped with a condenser and phosphorous oxychloride (153 g, 1 mol) was added dropwise at such a rate that gentle reflux was maintained. The solution turned yellow and some precipitate formed. After removal of the solvent and the tertiary amine, the residue was subjected to distillation under reduced pressure to give the crude product. Redistillation afforded a yellow liquid (158 g, 0.58 mmol, 58%). bp: 78–81 °C/28 Torr or 105–110 °C/50 Torr; IR (neat) 1600, 1506, 1250, 1164 cm−1; 1H NMR (CDCl3) δ 98.8 (s). Anal 3.84 (s, 3H), 6.94 (d, J = 9, 2H), 7.00 (d, J = 9, 2H); 19F NMR (CDCl3, C6F6 reference) δ 91.8.The related ring-substituted imines have been prepared by deoxygenation of isocyanate (eq 2),3 nucleophilic substitution of aromatic fluoride with imine (eq 3),4 and condensation of toluidine with 2,2,4,4-tetrakis(trifluoromethyl)-1,3-dithiacyclobutane (eq 4),5 respectively. (2)(3)(4)" @default.
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• W1874255178 date "2010-10-15" @default.
• W1874255178 modified "2023-09-26" @default.
• W1874255178 title "4-Methoxy-N-[2,2,2-trifluoro-1-(trifluoromethyl)ethylidene]-benzene" @default.
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• W1874255178 doi "https://doi.org/10.1002/047084289x.rn01154" @default.
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