The Journal of Organic Chemistry
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29.1, 28.8, 22.6, 14.1, 9.8. HRMS (ESI-TOF) m/z: [M]+ calcd for
C14H22OTe 336.0733; found 336.0708.
7.8 Hz, 2H), 1.68 (m, 2H), 1.23−1.33 (several peaks, 10H), 0.87 (t, J
= 6.9 Hz, 3H). 13C NMR (CDCl3): δ 158.5, 133.0, 105.3, 93.5, 31.7
(2C), 31.6, 31.5, 29.0, 28.7, 22.6, 14.0, 10.5. HRMS (ESI-TOF) m/z:
[M]+ calcd for C14H22O2Te 352.0682; found 352.0684.
2-(Hexadecyltelluro)phenol (5c). 2-Bromophenol (0.35 mL, 3
mmol), tert-BuLi (1.7 M in pentane, 5.3 mL, 9 mmol), and
dihexadecyl ditelluride (2.1 g, 3 mmol) were reacted in THF (20
mL) according to general procedure A. The mixture was purified by
flash chromatography (pentane/ethyl acetate = 95:5) to give the title
2-(Hexadecyltelluro)resorcinol (7c). 2-Bromoresorcinol (0.472 g,
2.5 mmol), tert-BuLi (1.7 M in pentane, 5.9 mL, 10 mmol), and
dihexadecyl ditelluride (1.8 g, 2.5 mmol) were reacted in THF (14
mL) according to general procedure A. The mixture was purified by
flash column chromatography (pentane/ethyl acetate = 95:5) to give
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compound as a pale yellow solid (0.308 g, 23%). Mp: 40−41 °C. H
NMR (CDCl3): δ 7.78 (dd, J = 1.6, 7.2 Hz, 1H), 7.29 (m, 1H), 7.06
(dd, J = 1.2, 8.4 Hz, 1H), 6.75 (m, 1H), 6.27 (s, 1H), 2.71 (t, J = 7.6
Hz, 2H), 1.70 (m, 2H), 1.18−1.32 (several peaks, 26H), 0.90 (t, J =
7.2 Hz, 3H). 13C NMR (CDCl3): δ 157.9, 142.1, 131.9, 121.2, 113.2,
101.3, 31.9, 31.7, 31.6, 29.7, 29.6 (2C), 29.5, 29.4 (2C), 28.8, 22.7,
14.1, 9.8. HRMS (ESI-TOF) m/z: [M]+ calcd for C22H38OTe
448.1985; found 448.1964.
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the title compound as a red solid (0.111 g, 10%). Mp: 61−63 °C. H
NMR (CDCl3): δ 7.19 (t, J = 8.0 Hz, 1H), 6.63 (d, J = 8.0 Hz, 2H),
6.09 (s, 2H), 2.60 (t, J = 8.0 Hz, 2H), 1.68 (m, 2H), 1.23−1.31
(several peaks, 26H), 0.89 (t, J = 7.2 Hz, 3H). 13C NMR (CDCl3): δ
158.5, 133.0, 105.3, 93.5, 31.9, 31.7, 31.6, 29.7, 29.6 (2C), 29.5, 29.4,
29.3, 28.8, 22.7, 14.1, 10.5. HRMS (ESI-TOF) m/z: [M]+ calcd for
C22H38O2Te 464.1934; found 464.1931.
2-(Butyltelluro)anisole (6a). 2-Bromoanisole (0.561 g, 3 mmol),
tert-BuLi (1.7 M in pentane, 3.5 mL, 6 mmol), and dibutyl ditelluride
(1.1 g, 3 mmol) were reacted in THF (20 mL) according to general
procedure A. The mixture was purified by flash chromatography
(pentane/ethyl acetate = 98:2) to give the title compound as a yellow
2-Bromo-3-(octyloxy)phenol (8). Potassium carbonate (6.04g, 43.8
mmol) was added to a solution of 2-bromoresorcinol (5.53 g, 29.2
mmol) and 1-bromooctane (5.04 g, 29.2 mmol) in anhydrous DMF
(100 mL) under nitrogen. After being stirred at 80 °C for 4 days, the
solution was quenched with water (50 mL) and extracted with ether
(50 mL × 3). The organic layer was dried over magnesium sulfate,
filtered, and evaporated under reduced pressure. The mixture was
purified by flash chromatography (pentane/ethyl acetate = 9:1) to give
the title compound as a colorless oil (2.4 g, 28%). 1H NMR (CDCl3):
δ 7.14 (t, J = 8.0 Hz, 1H), 6.66 (d, J = 8.0 Hz, 1H), 6.46 (d, J = 8.0 Hz,
1H), 5.62 (s, 1H), 4.01 (t, J = 6.4 Hz, 2H), 1.83 (m, 2H), 1.30−1.53
(several peaks, 10H), 0.89 (t, J = 7.2 Hz, 3H). 13C NMR (CDCl3): δ
156.0, 153.5, 128.5, 108.2, 104.6, 100.5, 69.2, 31.8, 29.3, 29.2, 29.1,
26.0, 22.6, 14.1. HRMS (ESI-TOF) m/z: [M + H]+ calcd for
C14H22BrO2 301.0803; found 301.0791.
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oil (0.675 g, 77%). H NMR (CDCl3): δ 7.41 (dd, J = 1.2, 7.6 Hz,
1H), 7.22 (td, J = 1.2, 7.6, 8.4 Hz, 1H), 6.87 (t, J = 7.6 Hz, 1H), 6.79
(d, J = 8.4 Hz, 1H), 3.86 (s, 3H), 2.88 (t, J = 7.6 Hz, 2H), 1.83 (m,
2H), 1.33 (m, 2H), 0.94 (t, J = 7.6 Hz, 3H). 13C NMR (CDCl3): δ
159.3, 134.3, 128.0, 122.0, 109.7, 103.9, 55.8, 33.5, 25.3, 13.4, 5.2.
HRMS (ESI-TOF) m/z: [M]+ calcd for C11H16OTe 294.0263; found
294.0233.
2-(Octyltelluro)anisole (6b). 2-Bromoanisole (0.374 g, 2 mmol),
tert-BuLi (1.7 M in pentane, 2.4 mL, 4 mmol), and dioctyl ditelluride
(0.963 g, 2 mmol) were reacted in THF (15 mL) according to general
procedure A. The mixture was purified by flash chromatography
(pentane/ethyl acetate = 98:2) to give the title compound as a yellow
2-(Butyltelluro)-3-(octyloxy)phenol (9a). 2-Bromo-3-(octyloxy)-
phenol (0.609 g, 2 mmol), tert-BuLi (1.7 M in pentane, 3.5 mL, 6
mmol), and dibutyl ditelluride (0.739 g, 2 mmol) were reacted in THF
(15 mL) according to general procedure A. The mixture was purified
by flash chromatography (pentane/ethyl acetate = 97.5:2.5) to give the
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oil (0.250 g, 36%). H NMR (CDCl3): δ 7.40 (dd, J = 1.2, 6.4 Hz,
1H), 7.21 (m, 1H), 6.87 (td, J = 0.9, 7.2 Hz, 1H), 6.79 (d, J = 8.1 Hz,
1H), 3.86 (s, 3H), 2.86 (t, J = 7.6 Hz, 2H), 1.81 (m, 2H), 1.27−1.43
(several peaks, 10H), 0.88 (t, J = 6.9 Hz, 3H). 13C NMR (CDCl3): δ
159.3, 134.4, 128.0, 122.0, 109.7, 103.9, 55.9, 32.2, 31.8, 31.5, 29.2,
29.0, 22.7, 14.1, 5.6. HRMS (ESI-TOF) m/z: [M]+ calcd for
C15H24OTe 350.0889; found 350.0875.
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title compound as a yellow oil (524 mg, 65%). H NMR (CDCl3): δ
7.20 (t, J = 8.0 Hz, 1H), 6.70 (dd, J = 0.8, 8.0 Hz, 1H), 6.53 (s, 1H),
6.38 (d, J = 8.0 Hz, 1H), 3.99 (t, J = 6.4 Hz, 2H), 2.68 (t, J = 7.6 Hz,
2H), 1.83 (m, 2H), 1.65 (m, 2H), 1.47 (m, 2H), 1.29−1.40 (several
peaks, 10H), 0.84−0.91 (several peaks, 6H). 13C NMR (CDCl3): δ
161.4, 159.0, 132.0, 106.0, 102.6, 93.2, 68.8, 33.7, 31.8, 29.3 (3C), 26.2,
24.9, 22.7, 14.1, 13.3, 8.5. HRMS (ESI-TOF) m/z: [M]+ calcd for
C18H30O2Te 408.1308; found 408.1332.
2-(Hexadecyltelluro)anisole (6c). 2-Bromoanisole (0.374 g, 2
mmol), tert-BuLi (1.7 M in pentane, 2.4 mL, 4 mmol), and
dihexadecyl ditelluride (1.4 g, 2 mmol) were reacted in THF (15
mL) according to general procedure A. The mixture was purified by
flash chromatography (pentane/ethyl acetate = 98:2) to give the title
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2-(Octyltelluro)-3-(octyloxy)phenol (9b). 2-Bromo-3-(octyloxy)-
phenol (0.609 g, 2 mmol), tert-BuLi (1.7 M in pentane, 3.5 mL, 6
mmol), and dibutyl ditelluride (0.963 g, 2 mmol) were reacted in THF
(15 mL) according to general procedure A. The mixture was purified
by flash chromatography (pentane/ethyl acetate = 97.5:2.5) to give the
compound as a pale yellow solid (0.397 g, 43%). Mp: 43−46 °C. H
NMR (CDCl3): δ 7.41 (dd, J = 1.6, 7.6 Hz, 1H), 7.20 (m, 1H), 6.89
(td, J = 0.8, 7.6 Hz, 1H), 6.79 (d, J = 8.0 Hz, 1H), 3.86 (s, 3H), 2.87 (t,
J = 7.6 Hz, 2H), 1.83 (m, 2H), 1.27−1.43 (several peaks, 26H), 0.89
(t, J = 7.2 Hz, 3H). 13C NMR (CDCl3): δ 159.3, 134.3, 128.0, 122.0,
109.7, 103.9, 55.8, 32.2, 31.9, 31.4, 29.7 (3C), 29.6, 29.5, 29.4, 29.0,
22.7, 14.1, 5.6. HRMS (ESI-TOF) m/z: [M]+ calcd for C23H40OTe
462,2141; found 462.2144.
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title compound as a yellow oil (0.490 g, 53%). H NMR (CDCl3): δ
7.20 (t, J = 8.1 Hz, 1H), 6.71 (dd, J = 0.9, 8.1 Hz, 1H), 6.54 (s, 1H),
6.38 (dd, J = 0.9, 8.1 Hz, 1H), 3.99 (t, J = 6.3 Hz, 2H), 2.68 (t, J = 7.8
Hz, 2H), 1.83 (m, 2H), 1.66 (m, 2H), 1.54 (m, 2H), 1.23−1.36
(several peaks, 20H), 0.86−0.93 (several peaks, 6H). 13C NMR
(CDCl3): δ 161.3, 159.0, 132.0, 106.0, 102.6, 93.2, 68.8, 31.8 (3C),
31.6, 29.3 (3C), 29.1, 28.8, 26.2, 22.7, 22.6, 14.1 (2C), 8.9. HRMS
(ESI-TOF) m/z: [M]+ calcd for C22H38O2Te 464.1934; found
464.1945.
2-(Butyltelluro)resorcinol (7a). 2-Bromoresorcinol (0.567 g, 3
mmol), tert-BuLi (1.7 M in pentane, 7.1 mL, 12 mmol), and dibutyl
ditelluride (2.2 g, 4.8 mmol) were reacted in THF (21 mL) according
to general procedure A. The mixture was purified by flash column
chromatography (pentane/ethyl acetate = 95:5) to give the title
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compound as a yellow oil (0.215 g, 24%). H NMR (CDCl3): δ 7.20
2-(Hexadecyltelluro)-3-(octyloxy)phenol (9c). 2-Bromo-3-
(octyloxy)phenol (0.609 g, 2 mmol), tert-BuLi (1.7 M in pentane,
3.5 mL, 6 mmol), and dihexadecyl ditelluride (1.4 g, 2 mmol) were
reacted in THF (15 mL) according to general procedure A. The
mixture was purified by flash chromatography (pentane/ethyl acetate
= 97.5:2.5) to give the title compound as a yellow oil (0.604 g, 53%).
1H NMR (CDCl3): δ 7.20 (t, J = 8.0 Hz, 1H), 6.70 (d, J = 8.0 Hz,
1H), 6.53 (s, 1H), 6.38 (d, J = 8.0 Hz, 1H), 3.99 (t, J = 6.4 Hz, 2H),
2.67 (t, J = 7.6 Hz, 2H), 1.83 (m, 2H), 1.65 (m, 2H), 1.40 (m, 2H),
1.22−1.34 (several peaks, 34H), 0.83−0.90 (several peaks, 6H). 13C
NMR (CDCl3): δ 161.4, 159.1, 132.0, 106.0, 102.6, 93.2, 68.8, 31.9,
31.8 (2C), 31.6, 29.7, 29.6 (2C), 29.5, 29.4, 29.3 (4C), 28.9, 26.2, 22.7,
(t, J = 8.0 Hz, 1H), 6.63 (d, J = 8.0 Hz, 2H), 6.07 (s, 2H), 2.60 (t, J =
7.6 Hz, 2H), 1.66 (m, 2H), 1.34 (m, 2H), 0.87 (t, J = 7.2 Hz, 3H). 13C
NMR (CDCl3): δ 158.5, 133.0, 105.3, 93.5, 33.7, 24.9, 13.3, 10.1.
HRMS (ESI-TOF) m/z: [M]+ calcd for C10H14O2Te 296.0056; found
296.0046.
2-(Octyltelluro)resorcinol (7b). 2-Bromoresorcinol (0.378 g, 2
mmol), tert-BuLi (1.7 M in pentane, 4.7 mL, 8 mmol), and dioctyl
ditelluride (1.9 g, 4 mmol) were reacted in THF (14 mL) according to
general procedure A. The mixture was purified by flash column
chromatography (pentane/ethyl acetate = 95:5) to give the title
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compound as a yellow oil (0.073 g, 10%). H NMR (CDCl3): δ 7.19
(t, J = 8.1 Hz, 1H), 6.63 (d, J = 8.1 Hz, 2H), 6.08 (s, 2H), 2.59 (t, J =
F
dx.doi.org/10.1021/jo400703w | J. Org. Chem. XXXX, XXX, XXX−XXX