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CAS No. : | 1211534-25-6 | MDL No. : | MFCD16609882 |
Formula : | C6H5BrClNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 222.47 | Pubchem ID : | 70700260 |
Synonyms : |
|
TPSA :Topological Polar Surface Area | 22.1 | H-Bond Acceptor Count : | 2 |
XLogP3 : | 2.5 | H-Bond Donor Count : | 0 |
SP3 : | 0.17 | Rotatable Bond Count : | 1 |
Signal Word: | Warning | Class | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
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Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With N-chloro-succinimide In N,N-dimethyl-formamide at 20℃; | To a solution of II (2.00 g, 10.6 mmol) in DMF (21 mL) was added NCS (2.98 g, 22.3 mmol). The reaction mixture was stirred at rt overnight. The reaction mixture was quenched with water, diluted with EtOAc, and the layers were separated. The aqueous layer was extracted with EtOAc and the combined organic extracts were washed with brine, dried over MgS04, and concentrated. The crude product was purified by silica chromatography to provide 1J (2.15 g, 9.18 mmol, 86percent yield) as a white solid. LC-MS Anal. Calc'd for C6H5BrClNO: 220.92, found [M+H] 223.8. 1H NMR (400 MHz, CDC13) δ 8.15 (s, 1H), 7.05 (s, 1H), 3.91 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | Stage #1: at 0 - 20℃; for 0.50 h; Stage #2: at 20 - 50℃; for 3.25 h; |
[00253j 27B. 4-Bromo-5-chloro-2-methoxypyridine: To MeOH (390 mL) at 0 °C was added TMS-C1 (49.0 mL, 386 mmol). The reaction mixture was warmed to rt and stirred for 30 mm. To this solution was added 27A (20.0 g, 96.0 mmol). The reaction mixturewas stirred for 15 mill and then NaNO2 (2.74 g, 39.8 mmol) was added to the mixture at rt. The reaction mixture was stirred at 50 °C for 3 h. The reaction mixture was concentrated. The residue was diluted with EtOAc and then basified to pH = 11-13 with 1 N aq. NaOH and extracted with EtOAc (3x). The combined organic layers wereconcentrated. Purification by recrystallization from MeOH and water afforded 27B as white needles (18.0 g, 81.0 mmol, 84percent yield). LC-MS Anal. Calc’d for C6H5BrC1NO:220.92, found [M+H] 223.9. |
84% | Stage #1: at 0 - 20℃; for 0.50 h; Stage #2: for 0.25 h; Stage #3: at 50℃; for 3.00 h; |
81B. 4-Bromo-5-chloro-2-methoxypyridine To MeOH (390 mL) was added chlorotrimethylsilane (49 mL, 386 mmol) at 0° C., and the solution was warmed to rt and stirred for 30 min. To the resulting solution was added 4-bromo-5-chloropyridin-2-amine (20 g, 96 mmol), and the mixture was stirred for 15 min. To the reaction mixture was added sodium nitrite (2.7 g, 40 mmol) and the solution was stirred at 50° C. for 3 h. The reaction mixture was evaporated in vacuo, and the residue was diluted with EtOAc. The pH of the aqueous layer was adjusted to pH=˜12 via addition of 1 N NaOH, and the solution was extracted 3* with EtOAc. The combined organic layers were concentrated, and the residue was purified via recrystallization from MeOH and H2O to give 4-bromo-5-chloro-2-methoxypyridine as white crystalline needles (18 g, 81 mmol, 84percent yield). LC-MS Anal. Calc'd for C6H5BrClNO 222.92. found [M+H] 223.9. 1H NMR (400 MHz, CDCl3) δ 8.18 (s, 1H), 7.08 (s, 1H), 3.94 (s, 4H). |
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