A Concise and Convenient Synthesis of 4-(Trifluoromethylthio)aniline

Gong, Shunze; Cai, Xinhong; Fu, Hao; Xu, Defeng

doi:10.14233/ajchem.2017.20138

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Decomposition Of Reagent1

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2018

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“…Solvent was evaporated in vacuo to provide the product 4. (4a): [17] Yellow viscous liquid. 41 mg (43 %).…”

Section: Decomposition Of Reagentmentioning

confidence: 99%

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Diversification of Trifluoromethylthiolation of Aromatic Molecules with Derivatives of Trifluoromethanesulfenamide

2018

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Trifluoromethylthiolation of aromatic compounds with different electrophilic reagents of the type ArNHSCF3 was studied in the presence of triflic acid as an activator. The effect of the reagent structure on the reactivity was studied with three different reagents: PhNHSCF3 (H/SCF3, 1a), 4‐ClC6H4NHSCF3 (Cl/SCF3, 1b) and C6F5NHSCF3 (F5/SCF3, 1c). p‐Chloro substituted reagent 1b was more stable than the unsubstituted 1a and was the most effective because it could not react by trifluoromethylthiolation of itself. This reaction was the most important side reaction of 1a. The pentafluoro derivative 1c was less reactive. Solvent played an important role in the transformation and, depending on the substrate, dichloromethane, hexane or trifluoroacetic acid gave the best yield of various trifluoromethylthiolated aromatic molecules (63–98 %).

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“…Solvent was evaporated in vacuo to provide the product 4. (4a): [17] Yellow viscous liquid. 41 mg (43 %).…”

Section: Decomposition Of Reagentmentioning

confidence: 99%

“…(4-Methoxyphenyl)(trifluoromethyl)sulfane (3a): [5s] (16), 69 (21), 45 (18). GC-MS (t = 6.38): m/z (%) = 208 (67) [M], 139 (100), 124 (12), 96 (14), 69 (17). Butyl)-2-[(trifluoromethyl)thio]phenol (3b): [12] (21), 188 (57), 175 (33), 124 (12), 96 (53), 69 (41), 45 (17).…”

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confidence: 99%