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3
3
3
3
(
d, J = 9.2 Hz, 2H), 7.75 (d, J = 8.8 Hz, 2H), 7.04 (d, J = 9.2 Hz, 2H), 6.88 (d, J = 8.8 Hz, 2H) ppm.
HH HH HH HH
13
C NMR (100 MHz, CDCl ): δ 163.2, 155.0, 143.7, 139.4, 126.3, 123.2, 117.0, 89.4 ppm.
3
28
1
-Methyl-4-(4-nitrophenoxy)benzene (Table 2, entry 10). Prepared according to procedure A, using 4ꢀ
methylphenol (227 mg, 2.1 mmol), 4ꢀfluoronitrobenzene (282 mg, 2.0 mmol), and 60% (w/w) CsF/CP (0.54 g)
in DMSO (5 mL) at 110 °C. After 0.15 h, the crude product was recrystallized in methanol to afford the final
1
product (435 mg, 95% yield) as an orange solid. mp: 69 °C (litt.: 69–70 °C). H NMR (300 MHz, DMSOꢀd6): δ
3
3
3
13
8
.22 (d, J = 9.2 Hz, 2H), 7.28 (d, J = 8.2 Hz, 2H), 7.06 (d, J = 8.8 Hz, 4H), 2.33 (s, 3H) ppm. C NMR
HH HH HH
(
75 MHz, DMSOꢀd6): δ 163.7, 152.3, 142.4, 135.3, 131.3, 126.6, 120.9, 117.4, 20.8 ppm.
46
1
-(tert-Butyl)-2-(4-nitrophenoxy)benzene (Table 2, entry 11). Prepared according to procedure A, using 2ꢀ
tertꢀbutylphenol (315 mg, 2.1 mmol), 4ꢀfluoronitrobenzene (282 mg, 2.0 mmol), and 60% (w/w) CsF/CP (0.54
g) in DMSO (5 mL) at 110 °C. After 0.75 h, the crude product was recrystallized in methanol to afford the final
1
product (531 mg, 98% yield) as a white solid. mp: 106 °C (litt.: 105–107 °C). H NMR (400 MHz, CDCl ): δ
3
3
3
3
3
8
.22 (d, J = 8.1 Hz, 2H), 7.49 (d, J = 7.8 Hz, 1H), 7.23 (m, 2H), 7.03 (d, J = 8.1 Hz, 2H), 6.91 (d, J
HH HH HH HH
13
=
7.8 Hz, 1H), 1.41 (s, 9H) ppm. C NMR (100 MHz, CDCl ): 163.8, 153.6, 142.9, 142.2, 128.3, 127.6, 126.7,
3
1
25.7, 121.6, 117.6, 35.2, 30.1 ppm.
-(tert-Butyl)-4-(4-nitrophenoxy)benzene (Table 2, entry 12). Prepared according to procedure A, using 4ꢀ
49
1
tertꢀbutylphenol (315 mg, 2.1 mmol), 4ꢀfluoronitrobenzene (282 mg, 2.0 mmol), and 60% (w/w) CsF/CP (0.54
g) in DMSO (5 mL) at 110 °C. After 0.5 h, the crude product was recrystallized in methanol to afford the final
1
3
product (514 mg, 95% yield) as a white solid. H NMR (300 MHz, CDCl ): δ 8.18 (d, J = 9.3 Hz, 2H), 7.42
3
HH
3
3
3
(
d, J = 9.3 Hz, 2H), 7.02 (d, J = 2.7 Hz, 2H), 6.99 (d, J = 2.7 Hz, 2H), 1.35 (s, 9H) ppm.
HH HH HH
4
5
1
3
,3-Dimethyl-5-(4-nitrophenoxy)benzene (Table 2, entry 13). Prepared according to procedure A, using
,5ꢀdimethylphenol (256 mg, 2.1 mmol), 4ꢀfluoronitrobenzene (282 mg, 2.0 mmol), and 60% (w/w) CsF/CP
(
0.54 g) in DMSO (5 mL) at 110 °C. After 0.5 h, the crude product was recrystallized in methanol to afford the
1
final product (461 mg, 95% yield) as a yellow solid. mp: 78 °C (litt.: 77–78 °C). H NMR (600 MHz, CDCl ): δ
3
3
3
13
8
.2 (d, J = 9.6 Hz, 2H), 7.01 (d, J = 9.6 Hz, 2H), 6.9 (brs, 1H), 6.7 (brs, 2H), 2.3 (s, 6H) ppm. C NMR
HH HH
(
150 MHz, CDCl ): 163.8, 154.9, 140.3, 127.4, 125.9, 118.3, 117.2, 113.2, 21.9 ppm.
3
4
6
1
2
,3-Di-tert-butyl-2-(4-nitrophenoxy)benzene (Table 2, entry 14). Prepared according to procedure A, using
,6ꢀdiꢀtertꢀbutylphenol (433 mg, 2.1 mmol), 4ꢀfluoronitrobenzene (282 mg, 2.0 mmol), and 60% (w/w) CsF/CP
16