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New Journal of Chemistry
Page 4 of 6
ARTICLE
Journal Name
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H); 13C NMR (100 MHz, CDCl3): 173.2, 157.4, 154.7, 144.7, 8.20 (s, 1 H), 8.02 (s, 1 H), 7.51 (dd, J = 8.6, 2.2 Hz,V1iewHA),rti7cl.e3O7n(lidne,
135.4, 126.0, 119.6, 118.0, 86.7, 20.5, 19.4.
J = 8.6 Hz, 1 H), 2.46 (s, 3 H); 13C NMR (1D00OIM: 10H.1z0,3C9D/DC0l3N)J:0107822.52G,
3‐Iodo‐7‐methoxy‐4H‐chromen‐4‐one (
2d).8c Yield 86% (51.9 154.3, 153.7, 136.0, 135.4, 125.6, 122.8, 117.9, 110.4, 20.9;
o
1
mg); white solid; mp 157‐158 C; H NMR (400 MHz, CDCl3): δ ESI‐HRMS Calcd for C10H8BrO2 [M + H]+ 238.9702, found
8.21 (s, 1 H), 8.13 (d, J = 9.0 Hz, 1 H), 6.99 (dd, J = 8.8, 2.4 Hz, 1 238.9699.
H), 6.83 (d, J = 2.4 Hz, 1 H), 3.91 (s, 3 H); 13C NMR (100 MHz, 3‐Bromo‐6,7‐dimethyl‐4
CDCl3): 172.6, 164.3, 157.9, 157.2, 128.1, 115.7, 115.3, 100.1, (32.8 mg); white solid; mp 141‐142 C; H NMR (400 MHz,
H
‐chromen‐4‐one
(
2n). Yield 65%
o
1
87.2, 55.9.
3‐Iodo‐4 ‐benzo[h]chromen‐4‐one
CDCl3): δ 8.16 (s, 1 H), 7.96 (s, 1 H), 7.22 (s, 1 H), 2.38 (s, 3 H),
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H
(
2e). Yield 45% (29.2 mg); 2.35 (s, 3 H); 13C NMR (100 MHz, CDCl3): 172.1, 154.6, 153.4,
o
1
white solid; mp 166‐167 C; H NMR (400 MHz, CDCl3): δ 8.42 144.8, 135.3, 125.8, 121.0, 118.1, 110.4, 20.4, 19.3; ESI‐HRMS
(s, 1 H), 8.38 (d, J = 8.2 Hz, 1 H), 8.11 (d, J = 8.8 Hz, 1 H), 7.90 (d, Calcd for C11H10BrO2 [M + H]+ 252.9859, found 252.9855.
J = 8.0 Hz, 1 H), 7.77‐7.64 (m, 3 H); 13C NMR (100 MHz, CDCl3): 3‐Bromo‐7‐methoxy‐4
H‐chromen‐4‐one (2o). Yield 63% (32.2
o
1
173.0, 156.8, 153.6, 135.8, 129.7, 128.2, 127.4, 126.1, 123.5, mg); white solid; mp 184‐185 C; H NMR (400 MHz, CDCl3): δ
122.2, 121.2, 118.0, 88.9; ESI‐HRMS Calcd for C13H8IO2 [M + H]+ 8.16 (d, J = 7.4 Hz, 2 H), 7.03‐6.98 (m, 1 H), 6.84 (d, J = 2.2 Hz, 1
322.9563, found 322.9558.
6‐Fluoro‐3‐iodo‐4 ‐chromen‐4‐one
H), 3.91 (s, 3 H); 13C NMR (100 MHz, CDCl3): 171.5, 164.4, 157.9,
H
(
2f).2a Yield 71% (41.2 mg); 153.2, 127.8, 117.0, 115.3, 110.8, 100.2, 55.9; ESI‐HRMS Calcd
o
1
white solid; mp 123‐124 C; H NMR (400 MHz, CDCl3): δ 8.30 for C10H8BrO3 [M + H]+ 254.9651, found 254.9647.
(s, 1 H), 7.92‐7.81 (m, 1 H), 7.53‐7.39 (m, 2 H); 13C NMR 3‐Bromo‐4
H‐benzo[h]chromen‐4‐one (2p). Yield 51% (27.9
(100MHz, CDCl3): 172.8, 159.8 (d, 1JC‐F = 247 Hz), 157.9, 152.4, mg); yellow solid; mp 133‐134 oC; 1H NMR (400 MHz, CDCl3): δ
122.8 (d, 3JC‐F = 8 Hz), 122.5 (d, 2JC‐F = 25 Hz), 120.3 (d, 3JC‐F = 8 8.42 (d, J = 8.2 Hz, 1 H), 8.38 (s, 1 H), 8.15 (d, J = 8.8 Hz, 1 H),
Hz), 111.4 (d, 2JC‐F = 24 Hz), 86.0.
6‐Chloro‐3‐iodo‐4 ‐chromen‐4‐one
7.92 (d, J = 8.0 Hz, 1 H), 7.78 (d, J = 8.8 Hz, 1 H), 7.73 (t, J = 7.2
H
(
2g). Yield 74% (45.3 mg); Hz, 1 H), 7.68 (t, J = 7.6 Hz, 1 H); 13C NMR (100 MHz, CDCl3):
o
1
white solid; mp 145‐146 C; H NMR (400 MHz, CDCl3): δ 8.30 172.0, 153.6, 152.9, 135.8, 129.7, 128.2, 127.5, 126.1, 123.6,
(s, 1 H), 8.18 (d, J = 2.4 Hz, 1 H), 7.65 (dd, J = 8.8, 2.4 Hz, 1 H), 122.2, 121.0, 119.4, 112.4; ESI‐HRMS Calcd for C13H8BrO2 [M +
7.44 (d, J = 8.8 Hz, 1 H); 13C NMR (100 MHz, CDCl3): 172.3, H]+ 274.9702, found 274.9697.
157.8, 154.5, 134.4, 131.8, 125.9, 122.5, 119.8, 86.6; ESI‐HRMS 3‐Bromo‐6‐fluoro‐4H‐chromen‐4‐one
(
2q). Yield 76% (36.7
mg); white solid; mp 134‐135 C; H NMR (400 MHz, CDCl3): δ
2h). Yield 57% (40.1 mg); 8.25 (s, 1 H), 7.88 (dd, J = 8.2, 3.0 Hz, 1 H), 7.52 (dd, J = 9.2, 4.2
white solid; mp 163‐164 C; H NMR (400 MHz, CDCl3): δ 8.26 Hz, 1 H), 7.48‐7.42 (m, 1 H); 13C NMR (100 MHz, CDCl3): 171.5,
o
1
Calcd for C9H5ClIO2 [M + H]+ 306.9017, found 306.9013.
6‐Bromo‐3‐iodo‐4 ‐chromen‐4‐one
H
(
o
1
1
3
(s, 1 H), 8.09 (d, J = 8.4 Hz, 1 H), 7.66 (d, J = 1.6 Hz, 1 H), 7.56 159.8 (d, JC‐F = 247 Hz), 153.9, 152.3, 124.2 (d, JC‐F = 8 Hz),
(dd, J = 8.4, 1.6 Hz, 1 H); 13C NMR (100 MHz, CDCl3): 172.6, 122.5 (d, 2JC‐F = 25 Hz), 120.4 (d, 3JC‐F = 8 Hz), 111.2 (d, 2JC‐F = 24
157.6, 156.1, 129.6, 128.5, 128.0, 121.1, 120.5, 87.1; ESI‐HRMS Hz), 110.1; ESI‐HRMS Calcd for C9H5BrFO2 [M + H]+ 242.9451,
Calcd for C9H5BrIO2 [M + H]+ 350.8512, found 350.8507.
7‐Bromo‐3‐iodo‐4 ‐chromen‐4‐one
found 242.9448.
2i). Yield 43% (30.2 mg); 3‐Bromo‐6‐chloro‐4H‐chromen‐4‐one (2r). Yield 72% (37.2
H
(
o
1
o
1
white solid; mp 163‐164 C; H NMR (400 MHz, CDCl3): δ 8.26 mg); white solid; mp 128‐129 C; H NMR (400 MHz, CDCl3): δ
(s, 1 H), 8.09 (d, J = 8.6 Hz, 1 H), 7.66 (d, J = 1.8 Hz, 1 H), 7.56 8.23 (s, 1 H), 8.22 (d, J = 2.6 Hz, 1 H), 7.65 (dd, J = 9.0, 2.6 Hz, 1
(dd, J = 8.6, 1.6 Hz, 1 H); 13C NMR (100 MHz, CDCl3): 172.6, H), 7.46 (d, J = 8.8 Hz, 1 H); 13C NMR (100 MHz, CDCl3): 171.1,
157.6, 156.1, 129.6, 128.5, 128.0, 121.1, 120.6, 87.1; ESI‐HRMS 154.4, 153.9, 134.4, 131.9, 125.7, 124.0, 119.9, 110.6; ESI‐
Calcd for C9H5BrIO2 [M + H]+ 350.8512, found 350.8507.
HRMS Calcd for C9H5BrClO2 [M + H]+ 258.9156, found 258.9152.
‐chromen‐4‐one 2s). Yield 77% (46.5 mg);
3‐Iodo‐6‐nitro‐4 ‐chromen‐4‐one 2j). Yield 31% (19.7 mg); 3,6‐Dibromo‐4
H
(
H
(
white solid; mp 93‐94 oC; 1H NMR (400 MHz, DMSO‐d6): δ 8.93 white solid; mp 141‐142 C; H NMR (400 MHz, CDCl3): δ 8.36
(s, 1 H), 8.73 (d, J = 2.8 Hz, 1 H), 8.58 (dd, J = 9.2, 2.8 Hz, 1 H), (d, J = 2.2 Hz, 1 H), 8.24 (s, 1 H), 7.79 (dd, J = 8.8, 2.2 Hz, 1 H),
7.94 (d, J = 9.2 Hz, 1 H); 13C NMR (100 MHz, DMSO‐d6): 172.8, 7.39 (d, J = 8.8 Hz, 1 H); 13C NMR (100 MHz, CDCl3): 170.9,
160.2, 159.1, 145.1, 129.1, 122.1, 121.4, 121.2, 87.6; APCI‐ 154.8, 153.9, 137.2, 128.9, 124.3, 120.1, 119.3, 110.7; APCI‐
o
1
HRMS Calcd for C9H5INO4 [M + H]+ 317.9258, found 317.9253.
HRMS Calcd for C9H5Br2O2 [M + H]+ 302.8651, found 302.8648.
‐chromen‐4‐one 2t). Yield 57% (34.4 mg);
6‐Chloro‐3‐iodo‐7‐methyl‐4 ‐chromen‐4‐one
H
(
2k).8a Yield 43% 3,7‐Dibromo‐4
H
(
o
1
o
1
(27.5 mg); white solid; mp 167‐168 C; H NMR (400 MHz, white solid; mp 143‐144 C; H NMR (400 MHz, CDCl3): δ 8.20
CDCl3): δ 8.25 (s, 1 H), 8.16 (s, 1 H), 7.34 (s, 1 H), 2.50 (s, 3 H); (s, 1 H), 8.12 (d, J = 8.6 Hz, 1 H), 7.68 (d, J = 1.6 Hz, 1 H), 7.58
13C NMR (100 MHz, CDCl3): 172.1, 157.6, 154.4, 143.6, 132.6, (dd, J = 8.6, 1.6 Hz, 1 H); 13C NMR (100 MHz, CDCl3): 171.5,
126.1, 120.7, 119.7, 86.5, 20.9.
3‐Bromo‐4 ‐chromen‐4‐one
156.0, 153.6, 129.6, 128.5, 127.8, 121.9, 121.2, 111.0; APCI‐
H
(
2l).7f Yield 80% (35.8 mg); white HRMS Calcd for C9H5Br2O2 [M + H]+ 302.8651, found 302.8647.
o
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solid; mp 94‐95 C; H NMR (400 MHz, CDCl3): δ 8.27 (dd, J = 3‐Bromo‐6‐nitro‐4H‐chromen‐4‐one (2u). Yield 35% (18.7 mg);
8.0, 1.6 Hz, 1 H), 8.24 (s, 1 H), 7.74‐7.70 (m, 1 H), 7.50‐7.44 (m, white solid; mp 110‐111oC; H NMR (400 MHz, DMSO‐d6): δ
1
2 H); 13C NMR (100 MHz, CDCl3): 172.2, 156.1, 153.8, 134.1, 8.99 (s, 1 H), 8.74 (d, J = 2.8 Hz, 1 H), 8.59 (dd, J = 9.2, 2.8 Hz, 1
126.4, 125.9, 123.1, 118.1, 110.7.
3‐Bromo‐6‐methyl‐4 ‐chromen‐4‐one
H), 7.96 (d, J = 9.2 Hz, 1 H); 13C NMR (100 MHz, DMSO‐d6):
2m). Yield 70% (33.3 171.2, 159.0, 156.7, 145.1, 129.1, 122.9, 121.9, 121.4, 110.4;
H
(
o
1
mg); white solid; mp 98‐99 C; H NMR (400 MHz, CDCl3): δ
4 | J. Name., 2012, 00, 1‐3
This journal is © The Royal Society of Chemistry 20xx
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