LETTER
Ciccarone, T. M.; MacTough, S. C.; Rooney, C. S.; Balani,
In Situ Synthesis of Mixed Diaryl Sulfides
877
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(17) (a) Typical Procedure: AgNO3 (0.17 g, 1 mmol), and
disulfide 1b (0.30 g, 1 mmol), were added to EtOH (1.0 mL)
and DMF (1.0 mL) and stirred at r.t. for 5 min. After that, β-
naphthol 2f (0.14 g, 1 mmol) was added. Then the contents
were refluxed with stirring for 10 h at 110 °C. The
precipitated silver mercaptide was filtered and the solvent
removed at reduced pressure. The residue obtained was
extracted with CH2Cl2 and dried over anhyd Na2SO4.
Removal of the CH2Cl2 under reduced pressure gave sulfide
3f which was purified by column chromatography (EtOAc–
hexane, 1:9).
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(b) Synthesis of Aryl Benzyl Thioethers 4: Silver
mercaptide (0.26 g, 1 mmol) and benzyl chloride (0.15 g, 1.2
mmol) in EtOH (5 mL) were refluxed for 6 h. Then NaOH
(0.2 g, 5 mmol) was added and reflux continued for an
additional 2 h. Upon cooling, NaOH (2 M, 30 mL) was
added to the reaction mixture followed by extraction with
CH2Cl2. The organic phase was washed with NaOH (2 M, 2
× 25 mL), H2O (25 mL) and brine (25 mL), dried over anhyd
Na2SO4, filtered and the solvent removed under reduced
pressure to give the aryl benzyl thioether.
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Representative Analytical Data; 1-(2-
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Nitrophenylthio)napthalen-2-ol (3f): The title compound
was prepared according to the typical procedure in 75%
yield (0.223 g) as a yellow solid (mp 170–171 °C). IR (KBr):
3435, 2905, 2845, 1588, 1545, 1497, 1335, 1055, 940, 865,
746, 689 cm–1. 1H NMR (400 MHz, CDCl3): δ = 8.27 (d, J =
7.9 Hz, 1 H), 8.16 (d, J = 8.6 Hz, 1 H), 7.86–7.97 (m, 6 H),
7.23 (s, 1 H), 6.84 (d, J = 7.6 Hz, 2 H). 13C NMR (100 MHz,
CDCl3): δ = 161.2, 156.3, 155.3, 153.1, 148.6, 143.5, 138.4,
136.7, 130.2, 129.1, 128.5, 127.2, 118.6, 117.4, 115.0.
HRMS (ESI): m/z [M + H+] calcd for C16H11NO3S:
298.0460; found: 298.0463. Anal. Calcd for C16H11NO3S: C,
64.63; H, 3.73; N, 4.71. Found: C, 64.58; H, 3.91; N, 4.88.
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© Georg Thieme Verlag Stuttgart · New York
Synlett 2013, 24, 873–877