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Organic & Biomolecular Chemistry
35.2, 31.0; HRMS (ESI-Orbitrap) m/z: [M + Na]+ calcd for (s, 1H), 3.24 (brs, 1H); 13C NMR (100 MHz, CDCl3) δ 143.7,
C23H24O3SNa 403.1338, found 403.1332. 141.2, 138.7, 138.2, 135.0, 134.1, 132.0, 130.9, 129.7, 129.6,
(2-((4-Bromophenyl)sulfonyl)phenyl)(phenyl)methanol (4i). 129.5, 129.3, 128.8, 128.3, 128.1, 127.9, 127.8, 127.3, 126.4,
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Colorless oil (46 mg, 57%); H NMR (400 MHz, CDCl3) δ 8.17 122.2, 70.1; HRMS (ESI-Orbitrap) m/z: [M + Na]+ calcd for
(dd, J = 7.9, 1.5 Hz, 1H), 7.64 (d, J = 8.7 Hz, 2H), 7.60–7.53 (m, C23H18O3SNa 397.0869, found 397.0868.
3H), 7.52–7.46 (m, 1H), 7.38 (dd, J = 7.7, 1.4 Hz, 1H), 7.25–7.21
(4-(tert-Butyl)phenyl)(2-tosylphenyl)methanol (4q). Yellow
(m, 3H), 7.10–7.05 (m, 2H), 6.58 (d, J = 3.1 Hz, 1H), 3.13 (d, J = oil (50 mg, 64%); 1H NMR (400 MHz, CDCl3) δ 8.16 (dd, J = 7.9,
4.1 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 143.6, 141.1, 140.5, 1.5 Hz, 1H), 7.71 (d, J = 8.3 Hz, 2H), 7.56–7.42 (m, 2H), 7.32 (d,
138.1, 134.4, 132.5, 130.9, 129.7, 128.8, 128.5, 128.4, 128.3, J = 7.6 Hz, 1H), 7.29–7.24 (m, 4H), 7.02 (d, J = 8.3 Hz, 2H), 6.56
127.5, 126.5, 70.2; HRMS (ESI-Orbitrap) m/z: [M + Na]+ calcd (s, 1H), 3.16 (brs, 1H), 2.40 (s, 3H), 1.28 (s, 9H); 13C NMR
for C19H1579BrO3SNa 424.9817, found 424.9810.
(100 MHz, CDCl3) δ 150.2, 144.3, 143.8, 138.9, 138.7, 138.3,
(2-((4-Chlorophenyl)sulfonyl)phenyl)(phenyl)methanol (4j). 134.0, 130.7, 129.9, 129.3, 128.1, 127.3, 126.1, 125.0, 69.8, 34.4,
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Colorless oil (36 mg, 50%); H NMR (400 MHz, CDCl3) δ 8.16 31.3, 21.6; HRMS (ESI-Orbitrap) m/z: [M + Na]+ calcd for
(d, J = 7.9 Hz, 1H), 7.72 (d, J = 8.5 Hz, 2H), 7.57 (dd, J = 14.8, C24H26O3SNa 417.1495, found 417.1492.
7.6 Hz, 1H), 7.49 (dd, J = 15.2, 7.6 Hz, 1H), 7.41 (d, J = 8.4 Hz,
(4-Methoxyphenyl)(2-tosylphenyl)methanol (4r). Yellow solid
2H), 7.37 (d, J = 7.7 Hz, 1H), 7.26–7.21 (m, 3H), 7.12–7.03 (m, (31 mg, 42%); mp 126–128 °C; 1H NMR (400 MHz, CDCl3) δ
2H), 6.58 (s, 1H), 3.15 (brs, 1H); 13C NMR (100 MHz, CDCl3) δ 8.15 (dd, J = 7.9, 1.5 Hz, 1H), 7.72 (d, J = 8.3 Hz, 2H), 7.55–7.42
143.6, 141.2, 140.0, 138.2, 134.4, 130.9, 129.64, 129.56(2C), (m, 2H), 7.33–7.24 (m, 3H), 7.01 (d, J = 8.7 Hz, 2H), 6.77 (d, J =
128.7, 128.4, 128.3, 127.5, 126.5, 70.2; HRMS (ESI-Orbitrap) m/ 8.7 Hz, 2H), 6.54 (d, J = 3.0 Hz, 1H), 3.78 (s, 3H), 3.14 (d, J = 3.8
z: [M + Na]+ calcd for C19H1535ClO3SNa 381.0323, found Hz, 1H), 2.41 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 158.8,
381.0314.
144.3, 143.9, 138.8, 138.5, 133.9, 133.5, 130.6, 129.9, 129.3,
(2-((4-Fluorophenyl)sulfonyl)phenyl)(phenyl)methanol (4k). 128.1, 127.6, 127.3, 113.5, 69.6, 55.2, 21.5; HRMS
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Colorless oil (41 mg, 60%); H NMR (400 MHz, CDCl3) δ 8.15 (ESI-Orbitrap) m/z: [M + Na]+ calcd for C21H20O4SNa 391.0975,
(dd, J = 7.9, 1.5 Hz, 1H), 7.81 (dd, J = 8.9, 5.0 Hz, 2H), found 391.0971.
7.58–7.45 (m, 2H), 7.35 (d, J = 7.7 Hz, 1H), 7.26–7.21 (m, 3H),
(4-Bromophenyl)(2-tosylphenyl)methanol (4s). Yellow solid
7.16–7.04 (m, 4H), 6.59 (d, J = 4.0 Hz, 1H), 3.23 (d, J = 4.2 Hz, (61 mg, 73%); mp 151–153 °C; IR (KBr) v (cm−1): 3498, 3045,
1H); 13C NMR (100 MHz, CDCl3) δ 165.3 (d, J = 257 Hz), 143.6, 1600, 1484, 1449, 1401, 1020, 814; H NMR (400 MHz, CDCl3)
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141.2, 138.4, 137.5 (d, J = 3.3 Hz), 134.3, 130.9, 130.2 (d, J = 9.5 δ 8.12 (dd, J = 7.8, 1.6 Hz, 1H), 7.68 (d, J = 8.4 Hz, 2H),
Hz), 129.5, 128.33, 128.25, 127.4, 126.4, 116.6 (d, J = 22.7 Hz), 7.55–7.43 (m, 2H), 7.33 (d, J = 8.5 Hz, 2H), 7.29–7.23 (m, 3H),
70.1; 19F NMR (376 MHz, CDCl3) δ −62.6; HRMS (ESI-Orbitrap) 6.95 (d, J = 8.5 Hz, 2H), 6.54 (s, 1H), 3.34 (brs, 1H), 2.41 (s,
m/z: [M + Na]+ calcd for C19H15FO3SNa 365.0618, found 3H); 13C NMR (100 MHz, CDCl3) δ 144.6, 143.0, 140.4, 139.1,
365.0612.
138.3, 134.0, 131.2, 130.7, 130.0, 129.4, 128.4, 128.2, 127.4,
Phenyl(2-(m-tolylsulfonyl)phenyl)methanol (4l). Colorless oil 121.3, 69.6, 21.6; HRMS (ESI-Orbitrap) m/z: [M + Na]+ calcd for
(46 mg, 68%); IR (KBr) v (cm−1): 3487, 3063, 2925, 1604, 1494, C20H1779BrO3SNa 438.9974, found 438.9966.
1450, 1042, 863; H NMR (400 MHz, CDCl3) δ 8.17 (dd, J = 7.8,
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(4-Chlorophenyl)(2-tosylphenyl)methanol (4t). White solid
1.6 Hz, 1H), 7.68–7.62 (m, 2H), 7.56–7.44 (m, 2H), 7.41–7.35 (53 mg, 71%); mp 147–149 °C; 1H NMR (400 MHz, CDCl3) δ
(m, 2H), 7.29–7.20 (m, 4H), 7.12–7.04 (m, 2H), 6.58 (d, J = 3.8 8.13 (dd, J = 7.9, 1.5 Hz, 1H), 7.70 (d, J = 8.1 Hz, 2H), 7.55–7.43
Hz, 1H), 3.24 (d, J = 4.0 Hz, 1H), 2.37 (s, 3H); 13C NMR (m, 2H), 7.30–7.24 (m, 3H), 7.18 (d, J = 8.4 Hz, 2H), 7.01 (d, J =
(100 MHz, CDCl3) δ 143.7, 141.4, 141.3, 139.7, 138.8, 134.2, 8.4 Hz, 2H), 6.56 (s, 1H), 3.30 (brs, 1H), 2.42 (s, 3H); 13C NMR
134.1, 130.9, 129.4, 129.2, 128.21, 128.16, 127.5, 127.3, 126.3, (100 MHz, CDCl3) δ 144.6, 143.1, 139.9, 139.1, 138.3, 134.0,
124.4, 69.9, 21.3; HRMS (ESI-Orbitrap) m/z: [M − H2O + H]+ 133.1, 130.7, 130.0, 129.4, 128.4, 128.3, 127.8, 127.4, 69.5, 21.6;
calcd for C20H17O2S 321.0944, found 321.0944.
HRMS (ESI-Orbitrap) m/z: [M + Na]+ calcd for C20H1735ClO3SNa
Phenyl(2-(o-tolylsulfonyl)phenyl)methanol (4m). Colorless 395.0479, found 395.0474.
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oil (27 mg, 40%); H NMR (400 MHz, CDCl3) δ 8.20–8.11 (m,
(4-Fluorophenyl)(2-tosylphenyl)methanol (4u). Colorless oil
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2H), 7.56–7.42 (m, 3H), 7.38 (dd, J = 15.2, 7.6 Hz, 1H), (48 mg, 68%); H NMR (400 MHz, CDCl3) δ 8.13 (dd, J = 7.8,
7.29–7.20 (m, 5H), 7.09–7.00 (m, 2H), 6.47 (s, 1H), 3.16 (brs, 1.5 Hz, 1H), 7.73 (d, J = 8.4 Hz, 2H), 7.56–7.43 (m, 2H),
1H), 2.42 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 143.7, 141.1, 7.31–7.23 (m, 3H), 7.07 (dd, J = 8.6, 5.5 Hz, 2H), 6.96–6.88 (m,
139.4, 138.5, 137.8, 134.1, 133.8, 132.8, 130.9, 129.4, 128.7, 2H), 6.57 (s, 1H), 3.24 (brs, 1H), 2.42 (s, 3H); 13C NMR
128.1, 127.8, 127.3, 126.7, 126.1, 69.4, 20.1; HRMS (100 MHz, CDCl3) δ 162.0 (d, J = 246 Hz), 144.5, 143.4, 139.0,
(ESI-Orbitrap) m/z: [M − H2O + H]+ calcd for C20H17O2S 138.4, 137.1, 134.0, 130.6, 130.0, 129.3, 128.3, 128.1 (d, J = 8.1
321.0944, found 321.0944.
Hz), 127.4, 115.0 (d, J = 21.5 Hz), 69.5, 21.6; 19F NMR
(2-(Naphthalen-2-ylsulfonyl)phenyl)(phenyl)methanol (4n). (376 MHz, CDCl3) δ −115; HRMS (ESI-Orbitrap) m/z: [M + Na]+
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Colorless oil (41 mg, 55%); H NMR (400 MHz, CDCl3) δ 8.46 calcd for C20H17FO3SNa 379.0775, found 379.0769.
(d, J = 1.9 Hz, 1H), 8.23 (dd, J = 7.7, 1.6 Hz, 1H), 7.96–7.85 (m,
(2-Tosylphenyl)(4-(trifluoromethyl)phenyl)methanol
(4v).
3H), 7.73 (dd, J = 8.7, 2.0 Hz, 1H), 7.68–7.45 (m, 4H), 7.31 (dd, White solid (54 mg, 67%); mp 152–153 °C; 1H NMR (400 MHz,
J = 7.6, 1.6 Hz, 1H), 7.17–7.09 (m, 3H), 7.07–7.02 (m, 2H), 6.68 CDCl3) δ 8.14 (dd, J = 7.8, 1.6 Hz, 1H), 7.71 (d, J = 8.3 Hz, 2H),
7070 | Org. Biomol. Chem., 2021, 19, 7066–7073
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