10.1002/chem.201702015
Chemistry - A European Journal
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GC-MS (EI, 70 eV): m/z (%) = 270 (47), 268 (44), 256 (13), 254 (12), 185
(100), 183 (97), 157 (63), 155 (64), 104 (17), 86 (47), 76 (73), 75 (59), 56
(90), 50 (42), 42 (30).
4-Bromo-N-butylbenzamide (9a)
White solid, 1H NMR (300 MHz, CDCl3): δ = 7.65-7.60 (2H, m), 7.58-
7.52 (2H, m), 6.19 (1H, brs), 3.43 (2H, td, J = 7.1, 5.6 Hz), 1.65-1.53 (2H,
m), 1.47-1.33 (2 H, m), 0.95 (3H, t, J = 7.3 Hz).
HRMS (ESI-TOF): calcd. for C11H1379BrNO2 [M + H]+ 270.01242, found
270.01266; calcd. for C11H1381BrNO2 [M
+
H]+ 272.01046, found
272.01078; calcd. for C11H1279BrNO2Na [M + Na]+ 291.99436, found
291.99469; calcd. for C11H1281BrNO2Na [M + Na]+ 293.9924, found
293.99276.
13C NMR (75 MHz, CDCl3): δ = 166.56, 133.67, 131.77, 131.75, 128.50,
125.96, 39.94, 31.71, 20.19, 13.81.
GC-MS (EI, 70 eV): m/z (%) = 257 (8), 255 (9), 228 (6), 226 (7), 215 (23),
214 (23), 213 (28), 212 (23), 185 (100), 183 (97), 157 (27), 155 (34), 105
(14), 104 (15), 75 (31), 41 (32).
6-(Morpholine-4-carbonyl)naphthalen-2-yl trifluoromethanesulfonate (3d)
White solid, 1H NMR (300 MHz, CDCl3): δ = 8.03 (1H, d, J = 1.8 Hz),
7.90-7.87 (1H, m), 7.77 (2H, ddd, J = 16.4, 8.6, 0.7 Hz), 7.61 (1 H, dd, J
= 8.7, 2.0 Hz), 7.51 (1 H, dd, J = 8.4, 1.7 Hz), 3.96- 3.38 (8H, m)
13C NMR (75 MHz, CDCl3): δ = 170.05, 134.73, 133.08, 131.16, 130.33,
130.02, 129.95, 127.57, 127.06, 125.35, 123.20 (q, J = 267 Hz), 66.94,
48.23, 42.87.
HRMS (ESI-TOF): calcd. for C11H1579BrNO [M + H]+ 256.03315, found
256.0337; calcd. for C11H1581BrNO [M + H]+ 258.03118, found 258.03139;
calcd. for C11H1479BrNONa [M + Na]+ 278.0151, found 278.01536; calcd.
for C11H1481BrNONa [M + Na]+ 280.01313, found 280.01338.
4-(((3s,5s,7s)-Adamantan-1-yl)carbamoyl)phenyl
trifluoromethanesulfonate (8b)
19F NMR (282 MHz, CDCl3): δ = -72.31
GC-MS (EI, 70 eV): m/z (%) = 389 (42), 388 (30), 361 (5), 303 (100), 256
(9), 211 (8), 170 (59), 142 (73), 114 (64), 86 (21), 69 (67), 56 (27).
HRMS (ESI-TOF): calcd. for C16H15F3NO5S [M + Na]+ 390.06175, found
390.06234; calcd. for C16H14F3NO5SNa [M + Na]+ 412.0437, found
412.04374.
White solid, 1H NMR (300 MHz, CDCl3): δ = 7.85-7.76 (2H, m), 7.36-
7.28 (2H, m), 5.76 (1H, brs), 2.11 (9H, s), 1.72 (6H, s).
13C NMR (75 MHz, CDCl3): δ = 164.88, 151.10, 136.38, 129.01, 121.49,
118.72 (q, J = 318.8 Hz), 52.75, 41.62, 36.32, 29.48
19F NMR (282 MHz, CDCl3): δ = -72.3
GC-MS (EI, 70 eV): m/z (%) = 403 (45), 346 (100), 310 (7), 270 (15), 253
(43), 213 (18), 189 (9), 161 (11), 120 (22), 92 (45), 79 (18), 69 (80)
(6-Bromonaphthalen-2-yl)(morpholino)methanone (4d)
White solid, 1H NMR (300 MHz, CDCl3): δ = 8.03 (1H, d, J = 1.9 Hz), 7.90
– 7.87 (1H, m), 7.80 (1H, d, J = 8.4 Hz), 7.74 (1H, d, J = 8.7 Hz), 7.61
(1H, dd, J = 8.8, 2.0), 7.51 (1H, dd, J = 8.4, 1.6 Hz), 3.97-3.38 (8 H, m).
13C NMR (75 MHz, CDCl3): δ = 170.05, 134.72, 133.08, 131.16, 130.33,
130.02, 129.94, 127.57, 127.06, 125.36, 124.99, 121.42, 66.94, 47.96,
42.35.
N-((3s,5s,7s)-Adamantan-1-yl)-4-bromobenzamide (9b)
White solid, 1H NMR (300 MHz, CDCl3): δ = 7.61-7.50 (4H, m), 5.74 (1H,
brs), 2.11 (9H, s), 1.72 (6 H, s).
13C NMR (75 MHz, CDCl3): δ = 165.59, 134.86, 131.63, 128.36, 125.59,
52.49, 41.63, 36.34, 29.48.
GC-MS (EI, 70 eV): m/z (%) = 321 (17), 319 (18), 235 (62), 233 (64), 207
(24), 205(24),154 (8), 126 (100), 56 (24).
GC-MS (EI, 70 eV): m/z (%) = 335 (39), 334 (24), 333 (40), 332 (16), 278
(71), 276 (69), 185 (100), 183 (99), 157 (42), 155 (44), 91 (26), 76 (23),
41 (26).
HRMS (ESI-TOF): calcd. for C15H1579BrNO2 [M + H]+ 320.02807, found
320.02817; calcd. for C15H1581BrNO2 [M
+
H]+ 322.02616, found
322.0264; calcd. for C15H1479BrNO2Na [M + Na]+ 342.01001, found
342.01019; calcd. for C15H1481BrNO2Na [M + Na]+ 344.00811, found
344.00823.
4-(Phenylcarbamoyl)phenyl trifluoromethanesulfonate (8c)
White solid, 1H NMR (300 MHz, CDCl3): δ = 7.98-7.92 (2H, m), 7.87 (1H,
brs), 7.62 (2H, dd, J = 8.7, 1.2 Hz), 7.42-7.35 (4H, m), 7.22-7.15 (1H, m).
13C NMR (75 MHz, CDCl3): δ = 164.08, 151.57, 137.43, 135.28, 129.36,
129.24, 125.13, 124.98, 121.88, 120.40, 118.73 (q, J = 318.8 Hz).
19F NMR (282 MHz, CDCl3): δ = -72.3
(1-Bromonaphthalen-2-yl)(morpholino)methanone (4e)
Viscous slurry, 1H NMR (300 MHz, CDCl3): δ = 8.29 (1 H, d, J = 8.4 Hz),
7.89- 7.82 (2H, m), 7.61 (2H, dddd, J = 21.6, 8.0, 6.9, 1.3 Hz), 7.31 (1H,
d, J = 8.3 Hz), 3.96-3.52 (6H, m), 3.35-3.15 (2H, m).
GC-MS (EI, 70 eV): m/z (%) = 345 (42), 253 (100), 184 (9), 161 (14), 120
(20), 92 (59), 69 (67).
13C NMR (75 MHz, CDCl3): δ = 168.25, 135.37, 134.11, 131.83, 128.82,
128.34, 128.29, 127.53, 127.30, 123.86, 119.53, 66.80, 66.69, 47.12,
42.03, 41.03.
HRMS (EI): calcd. for C14H10O4NF3S [M]+ 345.02771, found 345.02753.
4-Bromo-N-phenylbenzamide[4] (9c)
GC-MS (EI, 70 eV): m/z (%) = 321 (13), 319 (16), 235 (70), 233 (73), 207
(21), 205 (20), 155 (5), 126 (100), 86 (14), 56 (29).
HRMS (ESI-TOF): calcd. for C15H1579BrNO2 [M + H]+ 320.02807, found
White solid, 1H NMR (300 MHz, CDCl3): δ = 7.78-7.72 (3H, m), 7.67-7.60
(4H, m), 7.43-7.34 (2H, m), 7.21-7.14 (1H, m).
13C NMR (75 MHz, d6-DMSO): δ = 164.48, 138.90, 133.96, 131.35,
129.75, 128.59, 125.27, 123.78, 120.35.
320.0286; calcd. for C15H1581BrNO2 [M
+
H]+ 322.02616, found
322.02645; calcd. for C15H1479BrNO2Na [M + Na]+ 342.01001, found
342.01033; calcd. for C15H1481BrNO2Na [M + Na]+ 344.00811, found
344.00863.
GC-MS (EI, 70 eV): m/z (%) = 277 (28), 275 (26), 185 (99), 183 (100),
157 (43), 155 (49), 104 (9), 92 (40), 76 (42), 65 (65), 50 (25), 39 (24).
4-((2,6-Dimethylphenyl)carbamoyl)phenyl trifluoromethanesulfonate (8d)
White solid, 1H NMR (300 MHz, CDCl3): δ = 8.02-7.88 (2H, m), 7.68 (1H,
brs), 7.39-7.28 (2H, m), 7.21-7.07 (3H, m), 2.23 (6H, s).
13C NMR (75 MHz, CDCl3): δ = 164.31, 151.58, 135.55, 134.56, 133.51,
129.56, 128.40, 127.78, 121.76, 116.75 (q, J = 318.8 Hz), 18.44.
19F NMR (282 MHz, CDCl3): δ = -72.3
4-(Butylcarbamoyl)phenyl trifluoromethanesulfonate (8a)
White solid, 1H NMR (300 MHz, CDCl3): δ = 7.88-7.81 (2H, m), 7.37-
7.28 (2H, m), 6.25 (1H, brs), 3.45 (2H, td, J = 7.2, 5.7 Hz), 1.66-1.53 (2H,
m), 1.48-1.32 (2H, m), 0.95 (3H, t, J = 7.3 Hz).
13C NMR (75 MHz, CDCl3): δ = 165.83, 151.27, 135.16, 129.14, 121.58,
118.71 (q, J = 318.8 Hz), 40.06, 31.65, 20.16, 13.78.
GC-MS (EI, 70 eV): m/z (%) = 373 (40), 253 (100), 161 (15), 120 (85), 92
(39), 77 (20), 69 (69), 64 (20).
19F NMR (282 MHz, CDCl3): δ = -72.3
GC-MS (EI, 70 eV): m/z (%) = 325 (4), 310 (3), 296 (2), 283 (19), 282
(25), 253 (100), 192 (8), 161 (9), 120 (25), 92 (39), 69 (68), 41 (17).
HRMS (ESI-TOF): calcd. for C12H15F3NO4S [M + H]+ 326.06684, found
326.06725; calcd. for C12H14F3NO4SNa [M + Na]+ 348.04878, found
348.04929.
HRMS (ESI-TOF): calcd. for C16H15F3NO4S [M + H]+ 374.06684, found
374.06737; calcd. for C16H14F3NO4SNa [M + Na]+ 396.04878, found
396.04919
4-Bromo-N-(2,6-dimethylphenyl)benzamide (9d)
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