Structure of 139215-43-3
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CAS No. : | 139215-43-3 |
Formula : | C6H2Br2F2 |
M.W : | 271.88 |
SMILES Code : | FC1=CC(Br)=C(Br)C(F)=C1 |
MDL No. : | MFCD00042559 |
InChI Key : | GABNJPUNFZFOJE-UHFFFAOYSA-N |
Pubchem ID : | 2724517 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319 |
Precautionary Statements: | P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,4-dioxane; at 90℃; for 8h;Inert atmosphere; | General procedure: 4.15 2-Bromo-3,5-difluoro-4'-ethoxybiphenyl (4d): Starting with 1 (100 mg, 0.37 mmol), Cs2CO3 (119 mg, 0.37 mmol), Pd(PPh3)4 (3 mol%), 4-ethoxyphenylboronic acid (61 mg, 0.37 mmol), and 1,4-dioxane (4 mL), 4d was isolated as a colorless solid (74 mg, 65%). Mp 111-113 C. 1H NMR (300 MHz, CDCl3): δ = 1.44 (t, J = 6.95 Hz, 3H, CH3), 4.07 (q, J = 6.95, 3H, OCH3), 3.55 (s, 3H, OCH3), 6.83-6.97 (m, 3H, ArH), 7.28-7.34 (m, 3H, ArH). 13C NMR (62.89 MHz, CDCl3): δ = 14.8 (CH3), 63.5 (OCH2), 103.2 (t, J = 27.0 Hz, CH), 113.5 (d, J = 4.0 Hz, CH), 113.7 (dd, J = 22.2, 3.4 Hz, C), 114.1 (2CH), 128.4 (d, J = 6.9 Hz, CH), 128.7 (CH), 130.4 (CH), 133.7 (CH), 141.3 (d, J = 9.4 Hz, C), 159.0 (C), 159.3 (dd, JCF = 247.9, 13.3 Hz, CF), 161.3 (dd, JCF = 249.5, 13.3 Hz, CF). 19F NMR (282.4 MHz, CDCl3): δ = -101.8 (CF), -112.5 (CF). IR (ATR): , 2956 (w), 2926 (w), 2835 (w), 1616 (w), 1596 (w), 1503 (w), 1494 (w), 1455 (w), 1421 (w), 1338 (w), 1287 (w), 1247 (m), 1201 (w), 1180 (w), 1120 (w), 1089 (w), 1024 (m), 928 (w), 877 (w), 865 (w), 800 (w), 755 (w), 744 (m), 701 (w), 635 (w), 586 (m), 537 (w) cm-1. MS (EI, 70 eV): m/z (%) = 312 (61) (79Br) [M]+, 287 (12), 286 (98), 284 (100), 204(10). HRMS (EI) calcd. for C14H11O81BrF2 [M]+: 313.99354; found 313.99349. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,4-dioxane; at 90℃; for 8h;Inert atmosphere; | General procedure: 4.7 1,2-Di(4'-ethoxyphenyl)-3,5-difluorobenzene(3e): Starting with 1 (100 mg, 0.37 mmol), Cs2CO3 (263 mg, 0.81 mmol), Pd(PPh3)4 (3 mol%), 4-ethoxyphenylboronic acid (135 mg, 0.81 mmol), and 1,4-dioxane (4 mL) 3e was isolated as a colorless solid (88 mg, 68%). Mp 69-71 C. 1H NMR (300 MHz, CDCl3): δ = 1.36-1.43 (m, 4H, CH2), 3.94-4.03 (m, 6H, OCH3), 6.69-7.01 (m, 10H, ArH). 13C NMR (62.89 MHz, CDCl3): δ = 14.8 (CH3), 14.9 (CH3), 63.2 (OCH2), 63.3 (OCH2), 102.3 (t, J = 26.5 Hz, CH), 112 (dd, J = 21.8, 3.6 Hz, CH), 113.9 (2CH), 114.0 (2CH), 114.7 (2CH), 125.6 (C), 127.7 (C), 130.7 (2CH), 131.0 (C), 132.2 (C), 157.9 (C), 158.1 (C), 160.0 (dd, JCF = 249.2, 12.6 Hz, CF), 161.1 (dd, JCF = 249.2, 13.3 Hz, CF). 19F NMR (282.4 MHz, CDCl3): δ = -110.09 (CF), -112.02 (CF). IR (ATR, cm-1): , 3036 (w), 2975 (w), 2929 (w), 2873 (w), 1730 (w), 1605 (m), 1586 (m), 1511 (m), 1460 (m), 1432 (m), 1393 (m), 1335 (w), 1285 (m), 1239 (s), 1177 (m), 1110 (m), 1046 (m), 997 (m), 934 (w), 867 (m), 819 (s), 758 (m), 647 (w), 616 (m), 594 (w), 559 (m), 536 (m). MS (EI, 70 eV): m/z (%) = 354 (100) [M]+, 326 (21), 298 (30), 297 (22), 251 (24). HRMS (EI) calcd. for C22H20O2F2 [M]+: 354.14259; found 354.14230. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,4-dioxane; at 90℃; for 8h;Inert atmosphere; | General procedure: 4.8 1,2-Di(2',4'-dimethoxyphenyl)-3,5-difluorobenzene (3f): Starting with 1 (100 mg, 0.37 mmol), Cs2CO3 (263 mg, 0.81 mmol), Pd(PPh3)4 (3 mol%), <strong>[133730-34-4]2,4-dimethoxyphenylboronic acid</strong> (148 mg, 0.81 mmol), and 1,4-dioxane (4 mL), 3f was isolated as a colorless solid (81 mg, 58%). Mp 96-98 C. 1H NMR (300 MHz, CDCl3): δ = 3.44 (s, 3H, OCH3), 3.56 (s, 3H, OCH3), 3.68 (s, 3H, OCH3), 3.69 (s, 3H, OCH3), 6.20-6.30 (m, 3H, ArH), 6.72-6.85 (m, 3H, ArH), 7.29-7.42 (m, 1H, ArH), 761-766 (m, 1H, ArH). 13C NMR (62.89 MHz, CDCl3): δ = 55.0 (OCH3), 55.2 (OCH3), 55.3 (OCH3), 55.4 (OCH3), 98.1 (d, J = 12.7 Hz, CH), 98.9 (C), 102.4 (d, J = 109.9 Hz, C), 103.8 (d, J = 16.3 Hz, CH), 113.2 (d, J = 14.5 Hz, C), 113.8 (d, J = 16.5 Hz, CH), 115.8 (C), 121.2 (t, J = 9.25 Hz, C), 127.9 (t, J = 21.7 Hz, H), 130.2 (C), 131.4 (CH), 131.9 (C), 134.7 (t, J = 25.5 Hz, CH), 157.5 (d, J = 245.5 Hz, CF), 160.0 (C), 160.3 (C). 19F NMR (282.4 MHz, CDCl3): δ = -110.09 (CF), -113.03 (CF). IR (ATR, cm-1): , 2997 (w), 2921 (w), 2851 (w), 1607 (w), 1579 (w), 1508 (w), 1461 (w), 1435 (w), 1410 (w), 1337 (w), 1280 (w), 1205 (m), 1156 (m), 1124 (w), 1092 (m), 1030 (m), 981 (w), 935 (w), 830 (w), 647 (w), 723 (w), 692 (w), 613 (w), 588 (w), 540 (w). MS (EI, 70 eV): m/z (%) = 386 (100) [M]+, 355 (11). HRMS (EI) calcd. for C22H20O4F2 [M]+: 386.13242; found 386.13250. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,4-dioxane; at 90℃; for 8h;Inert atmosphere; | General procedure: 4.18 2-Bromo-3,5-difluoro-2',4'-dimethoxybiphenyl (4g): Starting with 1 (100 mg, 0.37 mmol), Cs2CO3 (119 mg, 0.37 mmol), Pd(PPh3)4 (3 mol%), <strong>[133730-34-4]2,4-dimethoxyphenylboronic acid</strong> (67 mg, 0.37 mmol), and 1,4-dioxane (4 mL), 4g was isolated as a colorless solid (81 mg, 67%). Mp. 64-66 C. 1H NMR (300 MHz, CDCl3): δ = 3.75 (s, 3H, OCH3), 3.89 (s, 3H, OCH3), 6.53-6.57 (m, 2H, Ar), 6.82-6.88 (m, 2H, Ar), 7.04 (d, J = 8.9 Hz, 1H, Ar). 13C NMR (75.46 MHz, CDCl3): δ = 55.4 (OCH3), 55.6 (OCH3), 98.7 (CH), 103.4 (t, J = 26.6 Hz, CH), 104 (CH), 106.9 (dd, J = 20.4, 4.0 Hz, C), 114.5 (dd, J = 22.3, 3.3 Hz, CH), 121.0 (t, J = 2.2, C), 131.1 (CH), 142.9 (d, J = 9.8 Hz, C), 157.4 (C), 159.22 (dd, JCF = 248.0, 13.7 Hz, CF), 161.3 (dd, JCF = 248.6, 13.2 Hz, CF), 161.4 (C). 19F NMR (282.4 MHz, CDCl3): δ = -100.5 (CF), -112.4 (CF). IR (ATR): , 3002 (w), 2958 (w), 2937 (w), 2836 (w), 1692 (s), 1785 (s), 1509 (s), 1463 (m), 1447 (m), 1468 (w), 1435 (s), 1345 (w), 1304 (s), 1281 (m), 1256 (m), 1206 (s), 1146 (m), 1127 (s), 1101 (s), 1031 (s), 997 (s), 924 (m), 833 (s), 796 (m), 716 (w), 637 (w), 599 (s), 587 (m) cm-1. MS (EI, 70 eV): m/z (%) = 330 (81Br) (95) [M]+, 328 (81Br) (93), 329 (15), 331 (14), 235 (15), 234 (100), 219 (35), 204 (12), 191 (20), 175 (26), 163 (13). ESI-HRMS calcd. for C14H1279BrF2O2 [M + H]+: 328.9983; found 328.9979. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | General procedure: 5.1 1-(4'-Methylphenyl)-2-(2",4"-dimethoyphenyl)-3,5-difluorobenzene (5a): Starting with 1 (200 mg, 0.74 mmol), Cs2CO3 (359 mg, 1.11 mmol), Pd(PPh3)4 (3 mol%), 4-methylboronic acid (100 mg, 0.74 mmol), <strong>[133730-34-4]2,4-dimethoxyphenylboronic acid</strong> (161 mg, 0.88 mmol), 1,4-dioxane (4 mL), and 5a was isolated as a colorless highly viscous oil (140 mg, 56%). 1H NMR (300 MHz, CDCl3): δ = 2.19 (s, 3H, CH3), 3.32 (s, 3H, OCH3), 3.69 (s, 3H, OCH3), 6.17 (d, J = 2.3 Hz, 1H, Ar), 6.32 (dd, J = 8.3, 2.3 Hz, 1H, Ar), 6.74-6.83 (m, 2H, Ar), 6.86-6.91 (m, 5H, Ar). 13C NMR (62.89 MHz, CDCl3): δ = 21.2 (CH3), 55.0 (OCH3), 55.3 (OCH3), 98.4 (CH), 102.5 (t, J = 26.3 Hz, CH), 104.1 (CH), 113.6 (dd, J = 21.9, 3.6 Hz, CH), 121.5 (t, J = 2.8 Hz, C), 125.7 (dd, J = 15.3, 3.6 Hz, C), 128.1 (2CH), 130.0 (2CH), 131.1 (C), 131.6 (CH), 136.4 (C), 141.2 (dd, J = 9.6, 4.5 Hz, C), 157.0 (C), 159.8 (dd, JCF = 246.8, 13.0 Hz, CF), 160.6 (C), 161.1 (dd, JCF = 247.1, 13.4 Hz, C). 19F NMR (282.4 MHz, CDCl3): δ = -111.86 (CF), -112.9 (CF). IR (ATR): , 2998 (w), 2956 (w), 2836 (w), 1736 (w), 1609 (s), 1586 (s), 1508 (s), 1454 (s), 1425 (m), 1401 (m), 1372 (w), 1303 (s), 1255 (m), 1184 (w), 1158 (s), 1145 (s), 1092 (s), 1032 (s), 996 (s), 925 (m), 861 (w), 834 (m), 818 (s), 796 (m), 736 (w), 718 (w), 663 (w), 607 (w), 587 (m) cm-1. MS (EI, 70 eV): m/z (%) = 340 (100) [M]+, 294 (11), 265 (13), 238 (12). ESI-HRM S calcd. for C21H19F2O2 [M + H]+: 341.1348; found 341.1348. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | General procedure: 5.6 1-(2',4'-Dimethoxyphenyl)-2-(4"-methylphenyl)-3,5-difluorobenzene (5f): Starting with 1 (200 mg, 0.74 mmol), Cs2CO3 (359 mg, 1.11 mmol), Pd(PPh3)4 (3 mol%), <strong>[133730-34-4]2,4-dimethoxyphenylboronic acid</strong> (134 mg, 0.74 mmol), 1,4-dioxane (4 mL), and 4-methylboronic acid (121 mg, 0.89 mmol), 5f was isolated as a colorless highly viscous oil (121 mg, 48%). 1H NMR (300 MHz, CDCl3): δ = 2.19 (s, 3H, CH3), 3.32 (s, 3H, OCH3), 3.69 (s, 3H, OCH3), 6.17 (d, J = 2.3 Hz, 1H, Ar), 6.32 (dd, J = 8.3, 2.3 Hz, 1H, Ar), 6.74-6.83 (m, 2H, Ar), 6.86-6.91 (m, 5H, Ar). 13C NMR (62.89 MHz, CDCl3): δ = 21.2 (CH3), 55.0 (OCH3), 55.3 (OCH3), 98.4 (CH), 102.5 (t, J = 26.3 Hz, CH), 104.1 (CH), 113.6 (dd, J = 21.9, 3.6 Hz, CH), 121.5 (t, J = 2.8 Hz, C), 125.7 (dd, J = 15.3, 3.6 Hz, C), 128.1 (2CH), 130.0 (2CH), 131.1 (C), 131.6 (CH), 136.4 (C), 141.2 (dd, J = 9.6, 4.5 Hz, C), 157.0 (C), 159.8 (dd, JCF = 246.8, 13.0 Hz, CF), 160.6 (C), 161.1 (dd, JCF = 247.1, 13.4 Hz, C). 19F NMR (282.4 MHz, CDCl3): δ = -111.86 (CF), -112.9 (CF). IR (ATR): , 2998 (w), 2956 (w), 2836 (w), 1736 (w), 1609 (s), 1586 (s), 1508 (s), 1454 (s), 1425 (m), 1401 (m), 1372 (w), 1303 (s), 1255 (m), 1184 (w), 1158 (s), 1145 (s), 1092 (s), 1032 (s), 996 (s), 925 (m), 861 (w), 834 (m), 818 (s), 796 (m), 736 (w), 718 (w), 663 (w), 607 (w), 587 (m) cm-1. MS (EI, 70 eV): m/z (%) = 340 (100) [M]+, 294 (11), 265 (13), 238 (12). ESI-HRMS calcd. for C21H19F2O2 [M + H]+: 341.1348; found 341.1348. |
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