R. J. Edsall, Jr. et al. / Bioorg. Med. Chem. 11 (2003) 3457–3474
3467
30-Chloro-1,10-biphenyl-4-ol (16). The title compound
was prepared by reacting 3-bromochlorobenzene (2.46 g,
12.85 mmol) with 4-tert-butyldimethylsilyloxyphenyl-
boronic acid (78) (4.5 g, 18.0 mmol) according to Method
C to yield 2.46 g (94%) of a light yellow solid: mp
(DMSO-d6): d 6.86 (2H, d, J=8.71 Hz), 7.37–7.40 (2H,
m), 7.50 (2H, d, J=8.71 Hz), 7.68 (2H, d, J=8.84 Hz),
9.62 (1H, s); 19F NMR (DMSO-d6): d ꢀ57.2 (s); MS
(EI) m/z 254.02 (M+). Anal. calcd for C13H9F3O2: C:
61.42H: 3.57; Found: C: 61.40H: 3.49.
ꢁ
1
59–60 C; H NMR (DMSO-d6): d 6.85 (2H, d, J=8.71
Hz), 7.31–7.34 (1H, m), 7.41–7.45 (1H, m), 7.50–7.56 (3,
m), 7.61–7.62 (1H, m), 9.64 (1H, s); MS (ESI) m/z 203/
1,10:30,100-Terphenyl-4-ol (31). The title compound was
prepared by reacting 3-bromobiphenyl (0.50 g, 2.15
mmol) with 4-tert-butyldimethylsilyloxyphenylboronic
acid (78) (0.76 g, 3.0 mmol) according to Method C to
.
205 ([MꢀH]ꢀ). Anal. calcd for C12H9ClO 0.10H2O:
C:69.81H:4.49; Found: C:69.71H:4.29.
yield 0.48 g (91%) of a white solid: mp78–85 ꢁC; H
1
1,10-Biphenyl-2,40-diol (18). The title compound was pre-
pared by reacting 2-bromophenol (0.42 g, 2.43 mmol)
with 4-tert-butyldimethylsilyloxyphenyl-boronic acid
(78) (0.85 g, 3.4 mmol) according to Method C to yield to
NMR (DMSO-d6): d 6.87 (2H, d, J=8.71 Hz),
7.46–7.52 (3H, m), 7.55–7.60 (4H, m), 7.74 (2H, d,
J=7.05 Hz), 7.80 (1H, m), 9.56 (1H, s); MS (EI) m/z
246.1 (M+). Anal. calcd for C18H14O 0.30H2O:
.
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1
yield 0.42 g (96%) of a white solid: mp150–155 C; H
NMR (DMSO-d6): d 6.77 (2H, d, J=8.71 Hz), 6.79–6.84
(1H, m), 6.89 (1H, dd, J=8.07 Hz, J=1.16 Hz), 7.06–
7.10 (1H, m), 7.18 (1H, dd, J=7.56 Hz, J=1.66 Hz), 7.35
C:85.89H:5.85; Found: C:85.58H:5.80.
1,10:40,100-Terphenyl-4-ol (32). The title compound was
prepared by reacting 4-bromophenol (0.49 g, 2.83 mmol)
with 4-biphenylboronic acid (0.79 g, 4.0 mmol) according
to Method C to yield 0.30 g (43%) of a white solid:
mp>250 ꢁC; 1H NMR (DMSO-d6): d 6.87 (2H, d,
J=8.71 Hz), 7.34–7.38 (1H, m), 7.46–7.49 (2H, m), 7.55
(2H, d, J=8.71 Hz), 9.32 (1H, s), 9.35 (1H, s); MS m/z
+
.
186.06 (M ). Anal. calcd for C12H10O2 0.10H2O:
C:76.66H:5.47; Found: C:76.76H:5.34.
1,10-Biphenyl-3,40-diol (19). The title compound was
prepared by reacting 3-bromophenol (0.82 g, 4.74
mmol) with 4-tert-butyldimethylsilyloxyphenylboronic
acid (78) (1.67 g, 6.6 mmol) according to Method C to
(2H, d, J=8.58 Hz), 7.66–7.72 (6H, m), 9.57 (1H, s); MS
+
.
(EI) m/z 246.1 (M ). Anal. calcd for C18H14O 0.10H2O:
C:87.14H:5.77; Found: C:87.30H:5.59.
yield 0.80g (91%) of a white solid: mp179–183 ꢁC; H
20-(Trifluoromethyl)-1,10-biphenyl-4-ol (33). The title
compound was prepared by reacting 2-bromobenzotri-
fluoride (0.61 g, 2.71 mmol) with 4-tert-butyldi-
methylsilyloxyphenylboronic acid (78) (0.96 g, 3.8
mmol) according to Method C to yield 0.37 g (57%) of
1
NMR (DMSO-d6): d 6.66–6.69 (1H, m), 6.82 (2H, d,
J=8.71 Hz), 6.92–6.93 (1H, m), 6.96–6.98 (1H, m),
7.16–7.20 (1H, m), 7.40 (2H, d, J=8.71 Hz), 9.40 (1H,
s), 9.49 (1H, s); MS (EI) m/z 186.06 (M+). Anal. calcd
for C12H10O2 0.10H2O: C: 76.66H:5.47; Found:
C:76.64H:5.48.
a white solid: mp47–49 ꢁC; H NMR (DMSO-d6): d
1
.
6.8.1 (2H, d, J=8.58 Hz), 7.11 (2H, d, J=8.33 Hz), 7.36
(1H, d, J=7.68 Hz), 7.53–7.57 (1H, m), 7.65–7.69 (1H,
m), 7.77–7.79 (1H, m), 9.58 (1H, s); 19F NMR (DMSO-
d6): d ꢀ55.8 (s); MS (EI) m/z 238.06 (M+). Anal. calcd
for C13H9F3O: C:65.55H:3.81; Found: C:65.30H:3.93.
20-Methoxy-1,10-biphenyl-4-ol (24). The title compound
was prepared by reacting 4-bromophenol (0.54 g, 3.12
mmol) with 2-methoxyphenylboronic acid (0.66 g, 4.4
mmol) according to Method C to yield 0.58 g (93%) of
a white solid: mp89–93 ꢁC; H NMR (DMSO-d6): d
30-(Trifluoromethyl)-1,10-biphenyl-4-ol (34). The title
compound was prepared by reacting 4-bromophenol
(0.54 g, 3.12 mmol) with 3-trifluoromethylphenylboronic
acid (0.83 g, 4.4 mmol) according to Method C to yield
1
3.74 (3H, s), 6.78 (2H, d, J=8.71 Hz), 6.96–7.00
(1H, m), 7.06 (1H, dd, J=8.26 Hz, J=0.83 Hz), 7.22
(1H, dd, J=7.49 Hz, J=1.73 Hz), 7.25–7.30 (3H, m),
9.41 (1H, s); MS (EI) m/z 200.08 (M+). Anal. calcd
0.44 g (59%) of a white solid: mp52–56 ꢁC; H NMR
1
.
for C13H12O2 0.10H2O:
C:77.35H:6.06.
C:77.28H:6.09;
Found:
(DMSO-d6): d 6.88 (2H, d, J=8.71 Hz), 7.58 (2H, d,
J=8.71 Hz), 7.61–7.67 (2H, m), 7.86–7.91 (2H, m), 9.68
(1H, s); MS (EI) m/z 238.06 (M+). Anal. calcd for
C13H9F3O: C:65.55H:3.81; Found: C:65.53H:3.78.
30-Methoxy-1,10-biphenyl-4-ol (25). The title compound
was prepared by reacting 4-bromophenol (0.61 g, 3.53
mmol) with 3-methoxyphenylboronic acid (0.75 g, 4.9
mmol), according to Method C to yield 0.31 g (44%) of
40-(Trifluoromethyl)-1,10-biphenyl-4-ol (35). The title
compound was prepared by reacting 4-bromobenzotri-
fluoride (0.60 g, 2.67 mmol) with 4-tert-butyldi-
methylsilyloxyphenylboronic acid (78) (0.94 g, 3.7
mmol) according to Method C to yield 0.40 g (63%) of
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1
a white solid: mp79–81 C; H NMR (DMSO-d6): d
3.80 (3H, s), 6.82–6.86 (3H, m), 7.08–7.09 (1H, m),
7.12–7.15 (1H, m), 7.29–7.33 (1H, m), 7.48 (2H, d,
J=8.71 Hz), 9.53 (1H, s); MS (EI) m/z 200.08 (M+).
Anal. calcd for C13H12O2: C: 77.98 H: 6.04; Found: C:
77.56 H: 5.91.
a white solid: mp129–132 ꢁC; H NMR (DMSO-d6):
1
d6.89 (2H, d, J=8.71 Hz), 7.58 (2H, d, J=8.72 Hz),
7.74 (2H, d, J=8.32 Hz), 7.80 (2H, d, J=8.20 Hz), 9.72
(1H, s); 19F NMR (DMSO-d6): d ꢀ61.2 (s); MS (EI) m/z
238.05 (M+). Anal. calcd for C13H9F3O: C:65.55H:3.81;
Found: C:65.11H:3.74.
40-(Trifluoromethoxy)-1,10-biphenyl-4-ol (29). The title
compound was prepared by reacting 4-bromophenol (0.52
g, 3.01 mmol) with 4-trifluoromethoxyphenylboronic acid
(0.87 g, 4.2 mmol) according to Method C to yield 0.53 g
(69%) of a white solid: mp124–127 ꢁC; 1H NMR
40-Hydroxy-1,10-biphenyl-2-carbonitrile (36). The title
compound was prepared by reacting 2-bromobenzonitrile