F
S. R. Dubbaka et al.
Paper
Synthesis
1-Methoxy-2-[(trifluoromethyl)thio]benzene (4m)11h
The yield (35%) of 4m was determined by 19F NMR spectroscopy.
19F NMR (CDCl3, 376 MHz): δ = –42.40 (s, 3 F).
The 19F NMR spectral data correspond to previously reported data.
GC-MS: m/z = 208 (M+).
Supporting Information
Supporting information for this article is available online at
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References
1-Methy-2-[(trifluoromethyl)thio]benzene (4n)23
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Compound 4n was isolated in 55% yield (21.2 mg).
1H NMR (CDCl3, 400 MHz): δ = 7.65 (d, J = 7.8 Hz, 1 H), 7.41–7.30 (m, 2
H), 7.24 (d, J = 7.4 Hz, 1 H), 2.54 (s, 3 H).
19F NMR (CDCl3, 376 MHz): δ = –42.89 (s, 3 F).
GC-MS: m/z = 192 (M+).
These spectroscopic data correspond to previously reported data.
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1-Methoxy-2-methyl-4-[(trifluoromethyl)thio]benzene (4o)31
Compound 4o was isolated in 62% yield (27.5 mg).
1H NMR (CDCl3, 400 MHz): δ = 7.65 (dd, J = 8.6, 2.2 Hz, 1 H), 7.40 (br d,
J = 2.2 Hz, 1 H), 6.83 (d, J = 8.5 Hz, 1 H), 3.86 (s, 3 H), 2.22 (s, 3 H).
19F NMR (CDCl3, 376 MHz): δ = –43.88 (s, 3 F).
GC-MS: m/z = 222 (M+).
These spectroscopic data correspond to previously reported data.
1-Methoxy-2-chloro-4-[(trifluoromethyl)thio]benzene (4p)16
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Compound 4p was isolated in 70% yield (33.9 mg).
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1H NMR (CDCl3, 400 MHz): δ = 7.67 (d, J = 2.2 Hz, 1 H), 7.53 (dd, J = 8.6,
2.2 Hz, 1 H), 6.95 (d, J = 8.6 Hz, 1 H), 3.94 (s, 3 H).
19F NMR (CDCl3, 376 M Hz): δ = –43.56 (s, 3 F).
GC-MS: m/z = 242 (M+).
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Jiang, X. Adv. Synth. Catal. 2013, 355, 617.
These spectroscopic data correspond to previously reported data.
4-[(Trifluoromethyl)thio]pyridine (4q)23
The yield (33%) of 4q was determined by 19F NMR spectroscopy.
19F NMR (CDCl3, 376 MHz): δ = –40.45.
The 19F NMR spectral data correspond to previously reported data.
GC-MS: m/z = 179 (M+).
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2-Methoxy-3-[(trifluoromethyl)thio]pyridine (4r)24a
The yield (26%) of 4r was determined by 19F NMR spectroscopy.
19F NMR (CDCl3, 376 MHz): δ = –43.88.
The 19F NMR spectral data correspond to previously reported data.
GC-MS: m/z = 209 (M+).
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Acknowledgment
We thank Dr. Sergei Belyakov for his support and suggestions towards
this manuscript, and Dr. Thresen Mathew and Dr. Matthew
Isherwood for their careful and valuable correction of this manu-
script.
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2016, 48, A–G