D
Y. Xie et al.
Letter
Synlett
Supporting Information
(8) Moorthy, J. N.; Senapati, K.; Parida, K. N.; Jhulki, S.; Sooraj, K.;
Nair, N. N. J. Org. Chem. 2011, 76, 9593.
Supporting information for this article is available online at
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Select 2017, 2, 1620.
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References and Notes
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(15) The composition of the byproduct mixture was rather compli-
cated. The main byproduct, (phenylsulfanyl)methyl acetate was
isolated in 37% yield.
(16) Sulfoxides 2; General Procedure
A 25 mL glass tube was charged with the appropriate sulfide 1
(1 mmol), MeOH (0.5 mL), and CH2Cl2 (4.5 mL). AlCl3 (0.5 mmol)
was added, and the mixture was stirred at r.t. for 1 min.
PhI(OAc)2 (1.0 equiv) was then added and the solution was
stirred at r.t. until the sulfide was consumed (TLC). The solvent
was removed under reduced pressure and the crude product
was purified by column chromatography [silica gel (200–300
mesh), EtOAc–PE].
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4081.
Methyl Phenyl Sulfoxide (2a)
Colorless oil; yield: 138.6 mg (99%). 1H NMR (400 MHz, CDCl3):
δ = 7.65 (dd, J = 7.8, 1.8 Hz, 2 H), 7.56–7.47 (m, 3 H), 2.72 (s, 3
H). 13C NMR (101 MHz, CDCl3): δ = 145.33, 130.99, 129.28,
123.41, 43.71. MS (ESI): m/z [M + H]+ calcd for C7H9OS: 141.0;
found: 141.0.
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49, 917.
4-Fluorophenyl Methyl Sulfoxide (2b)
Colorless oil; yield: 132.7 mg (84%). 1H NMR (400 MHz, CDCl3):
δ = 7.70–7.63 (m, 2 H), 7.28–7.21 (m, 2 H), 2.73 (s, 3 H). 13C NMR
(101 MHz, CDCl3): δ = 165.47, 162.97, 140.94, 125.88, 125.80,
116.73, 116.50, 43.97. MS (ESI): m/z [M + H]+ calcd for C7H8FOS:
159.0; found: 158.8.
4-Chlorophenyl Methyl Sulfoxide (2c)
Colorless oil; yield: 160.1 mg (92%). 1H NMR (400 MHz, CDCl3):
δ = 7.59 (d, J = 8.4 Hz, 2 H), 7.51 (d, J = 8.6 Hz, 2 H), 2.72 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 144.05, 137.06, 129.52, 124.92,
43.84. MS (ESI): m/z [M + H]+ calcd for C7H8ClOS: 175.0; found:
175.1.
4-Bromophenyl Methyl Sulfoxide (2d)
White solid; yield: 189.7 mg (87%); mp 79–81°C. H NMR (400
1
MHz, CDCl3): δ = 7.65 (d, J = 8.5 Hz, 2 H), 7.51 (d, J = 8.5 Hz, 2 H),
2.70 (s, 3 H). 13C NMR (101 MHz, CDCl3): δ = 144.85, 132.58,
125.47, 125.19, 44.00. MS (ESI): m/z [M
+
H]+ calcd for
C7H8BrOS: 218.9; found: 218.9.
© Georg Thieme Verlag Stuttgart · New York — Synlett 2017, 28, A–D