The Journal of Organic Chemistry
Page 14 of 23
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Pentafluorophenyl benzoate 9f. Pale yellow solid (2.26 g, 98% yield). 19F{1H} NMR (CDCl3, 377
MHz) -152.4 (dm, 2F, J = 17.3 Hz), -157.9 (t, 1F, J = 21.7 Hz), -162.3 (ddm, 2F, J = 21.8 Hz, 17.3
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Hz). H NMR (CDCl3, 400 MHz) 8.24 – 8.18 (m, 2H), 7.75 – 7.68 (m, 1H), 7.59 – 7.52 (m, 2H).
13C{1H} NMR (CDCl3,101 MHz) 162.6, 141.3 (dm, 2C, J = 252.3 Hz), 139.4 (dtt, 1C, J = 252.6 Hz,
J = 13.2 Hz, J = 4.1 Hz), 139.2 (dm, 2C, J = 252.8 Hz), 134.8, 130.8 (2C), 128.9 (2C), 125.1 (tdt, 1C, J
= 14.5 Hz, J = 4.3 Hz, J = 2.0 Hz), 19.7. These data are in agreement with those previously reported. 22
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Pentafluorophenyl 4-methylbenzoate 9i. Pale yellow oil (2.39 g, 99% yield). 19F{1H} NMR (CDCl3,
377 MHz) -152.6 (dm, 2F, J = 17.2 Hz), -158.3 (t, 1F, J = 21.7 Hz), -162.4 – 162.7 (m, 2F). 1H NMR
(CDCl3, 400 MHz) 8.09 (d, 2H, J = 8.2 Hz), 7.35 (d, 2H, J = 8.0 Hz), 2.48 (s, 3H). 13C{1H} NMR
(CDCl3,101 MHz) 162.5, 141.4 (dm, 2C, J = 252.3 Hz), 139.5 (dm, 1C, J = 253.0 Hz), 138.0 (dm, 2C,
J = 254.3 Hz), 130.8 (2C), 129.6 (2C), 125.7 – 125.2 (m, 1C), 145.9, 124.2, 21.8. MS (ESI+) m/z: 303.04
[M+H]+. HRMS (ESI+) m/z: [M+H]+ Calcd. for [C14H8F5O2]: 303.0439, found: 303.0439.
Pentafluorophenyl 2-methylbenzoate 9g. White solid (2.39 g, 99% yield). 19F{1H} NMR (CDCl3, 377
MHz) -152.5 (dm, 2F, J = 22.1 Hz), -158.4 (t, 1F, J = 21.6 Hz), -162.5 – 162.7 (ddm, 2F, J = 21.6 Hz,
17.3 Hz). 1H NMR (CDCl3, 400 MHz) 8.19 (dd, 1H, J = 8.2 Hz, J = 1.4 Hz), 7.55 (dd, 1H, J = 7.6 Hz,
J = 1.4 Hz), 7.42 – 7.32 (m, 2H), 2.66 (s, 3H). 13C{1H} NMR (CDCl3,101 MHz) 162.8, 142.3, 141.5
(dm, 2C, J = 251.5 Hz), 139.5 (dm, 1C, J = 253.1 Hz), 139.2 (dm, 2C, J = 253.4 Hz), 133.8, 132.2,
131.7, 126.2, 125.6 – 125.2 (m, 1C), 126.0, 21.7. MS (ESI+) m/z: 303.04 [M+H]+. HRMS (ESI+) m/z:
[M+H]+ Calcd. for [C14H8F5O2]: 303.0439, found: 303.0438.
Pentafluorophenyl 4-(trifluoromethoxy)benzoate 9n. White solid (2.95 g, 99% yield). 19F {1H} NMR
(CDCl3, 377 MHz) -57.6 (s, 3F), -152.4 (dm, 2F, J = 17.3 Hz), -157.4 (t, 1F, J = 21.7 Hz), -162.0 (ddm,
2F, J = 21.2 Hz, J =17.5 Hz). 19F NMR (CDCl3, 377 MHz) -57.6 (bs), -152.4 (dm, 2F, J = 17.3 Hz), -
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157.4 (t, 1F, J = 21.7 Hz), -162.0 (ddm, 2F, J = 21.2 Hz, J =17.5 Hz). H NMR (CDCl3, 400 MHz)
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8.27 (d, 2H, J = 8.8 Hz), 7. 38 (d, 2H, J = 8.5 Hz). C{1H}NMR (CDCl3,101 MHz) 161.4, 154.0,
141.4 (dm, 2C, J = 253.8 Hz), 139.7 (dm, 1C, J = 255.5 Hz), 138.0 (dm, 2C, J = 252.2 Hz), 132.9 (2C),
125.5 – 124.9 (m, 1C), 125.2, 120.6 (2C), 120.3 (q, 1C, J = 259.5 Hz). MS (ESI+) m/z: 373.02 [M+H]+.
HRMS (ESI+) m/z: [M+H]+ Calcd. for [C14H5F8O3]: 373.0105, found: 373.0104.
Pentafluorophenyl 4-methoxybenzoate 9m. White solid (2.49 g, 98% yield). 19F{1H} NMR (CDCl3,
377 MHz) -152.6 (dm, 2F, J = 17.2 Hz), -158.5 (t, 1F, J = 21.7 Hz), -162.7 (ddm, 2F, J = 21.9 Hz, J
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=17.1 Hz). H NMR (CDCl3, 400 MHz) 8.15 (d, 2H, J = 8.7 Hz), 7.01 (d, 2H, J = 8.8 Hz), 3.91 (s,
3H). 13C{1H} NMR (CDCl3,101 MHz) 164.8, 162.3, 141.4 (dm, 2C, J = 255.9 Hz), 139.4 (dm, 1C, J
= 253.0 Hz), 137.9 (dm, 2C, J = 251.6 Hz), 133.0 (2C), 125.8 – 125.3 (m, 1C), 119.1, 114.2 (2C), 55.6.
These data are in agreement with those previously reported.23
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