BULLETIN OF THE
Note
KOREAN CHEMICAL SOCIETY
in CDCl3 with TMS as an internal standard. Crystallographic
data were collected on a Bruker SMART APEX-II CCD dif-
fractometer (Brucker, Ettlingen, Germany). CCDC reference
number is 1037698 for 1. The data can be obtained free of
charge from The Cambridge Crystallographic Data Centre
3H, CH3). 13C NMR (100 MHz, CDCl3): 158.3, 157.0,
141.8, 139.7, 137.1, 128.7, 127.3, 126.0, 125.6, 121.8,
118.1, 64.7, 24.5.
[3-(4,6-Dimethylpyrimidin-2-yl)phenyl]methanol (2o):
Yield 81%. Anal. Calcd. for C13H14N2O: C,
72.87; H, 6.59; N, 13.07. Found: C, 72.98; H, 6.46; N,
1
[(C4N2HCl2)2Pd2(PPh3)2I2] (1). A reaction mixture of
Pd(PPh3)4 (0.2 mmol), 2,4,6-trichloropyrimidine (0.2 mmol),
and NaI (0.3 mmol) in toluene (10 mL) was refluxed
under nitrogen atmosphere for 3 h and then cooled to room
temperature. Purification by flash chromatography gave the
complex 1. Red solid, 52% yield. Anal. Calcd. for
C44H32Cl4I2N4P2Pd2: C, 41.06; H, 2.51; N, 4.35. Found: C,
13.21. MS-ESI+ [m/z]: 215.1 (M + H) +. H NMR. (400
MHz, CDCl3): δ 8.18–8.22 (m, 2H, ArH), 7.30 (s, 2H,
ArH), 6.80 (s, 1H, ArH), 4.59 (s, 2H, CH2), 3.22 (s, 1H,
OH), 2.41 (s, 6H, CH3). 13C NMR (100 MHz, CDCl3):
166.9, 164.1, 141.4, 138.1, 128.9, 128.7, 127.4, 126.7,
118.1, 65.0, 24.1.
1
41.29; H, 2.33; N, 4.52. H NMR (400 MHz, CDCl3): δ
Acknowledgments. This work was supported by the
Innovation Scientists and Technicians Troop Construction
Projects of Henan Province, and the Science Foundation
of Henan Education Department (Nos. 15B150008 and
14A150049).
7.72–7.81 (12H, m, ArH), 7.28–7.42 (20H, m, PyH + ArH).
MS-ESI+ [m/z]: 1029.9 (M – 2I)2+.
General Procedure for the Suzuki Coupling.
A
Schlenk tube was charged with the prescribed amount of cat-
alyst, aryl halide (1.0 mmol), 3-(hydroxymethyl)phenylboro-
nic acid (1.5 mmol), TBAB (1.0 mmol), the selected
base (3.0 mmol), and water under nitrogen atmosphere. The
reaction mixture was heated at 100 ꢀC for 12 h. After cooling,
the mixture was extracted with CH2Cl2, the solvent was eva-
porated, and the product was separated by passing through
a silica gel column with CH2Cl2/ethyl acetate (5:1) as
eluent. The products 2f, 2j, 2l, and 2o were new compounds
and were determined by 1H and C13 NMR. Other
products were characterized by comparison with data in the
literature.9
SupportingInformation. Additionalsupportinginformation
is available in the online version of this article.
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40-Acetyl-biphenyl-3-methanol (2f ): Yield 92% (based
on p-CH3CO(C6H4)Br). Anal. Calcd. for C15H14O2: C,
79.62; H, 6.24. Found: C, 79.85; H, 6.09. MS-ESI+ [m/z]:
1
226.1 (M+). H NMR. (400 MHz, CDCl3): δ 7.99 (d, J =
6.8 Hz, 2H, ArH), 7.66 (d, J = 6.8 Hz, 2H, ArH), 7.62 (s,
1H, ArH), 7.53 (d, J = 6.0 Hz, 1H, ArH), 7.44 (t, J = 6.0 Hz,
1H, ArH), 7.26 (s, 1H, ArH), 4.77 (s, 2H, CH2), 3.16 (s,
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[3-(4-Methylpyridin-2-yl)phenyl]methanol (2j): Yield
83%. Anal. Calcd. for C13H13NO: C, 78.36; H, 6.58; N,
7.03. Found: C, 78.25; H, 6.47; N, 7.21. MS-ESI+ [m/z]:
1
200.1 (M + H)+. H NMR. (400 MHz, CDCl3): δ 7.93 (s,
1H, ArH), 7.84 (m, 1H, ArH), 7.53 (s, 1H, ArH), 7.38–7.42
(m, 2H, ArH), 7.06 (s, 1H, ArH), 4.72 (s, 2H, CH2), 2.82
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CDCl3): 157.2, 149.2, 148.0, 141.6, 139.7, 128.9, 127.4,
126.1, 125.8, 123.3, 121.8, 65.1, 21.2.
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7.03. Found: C, 78.48; H, 6.43; N, 7.19. MS-ESI+ [m/z]:
1
200.1 (M + H)+. H NMR. (400 MHz, CDCl3): δ 7.77 (s,
1H, ArH), 7.67 (d, J = 6.0 Hz, 1H, ArH), 7.48 (t, J = 6.0 Hz,
1H, ArH), 7.32 (d, J = 6.0 Hz, 1H, ArH), 7.25 (t, J = 6.0 Hz,
1H, ArH), 7.18 (t, J = 6.0 Hz, 1H, ArH), 6.96 (t, J = 6.0 Hz,
1H, ArH), 4.52 (s, 2H, CH2), 3.70 (br, 1H, OH), 2.50 (s,
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Bull. Korean Chem. Soc. 2015, Vol. 36, 2355–2358
© 2015 Korean Chemical Society, Seoul & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim