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CAS No. : | 886364-86-9 | MDL No. : | MFCD07375090 |
Formula : | C7H5BrN2 | Boiling Point : | 293.3°C at 760 mmHg |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 197.03 g/mol | Pubchem ID : | 53395468 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | at 158℃; for 3 h; sealed vessel | 2,5-Dibromo-4-methylpyridine(5.0 g, 19.9 mmol), copper cyanide (1.43 g, 15.9 mmol), sodium cyanide (0.801 g, 16.3 mmol) and dimethylformamide (30 mL) were combined in a sealed reaction vessel and heated at 158 0C for 3 h. The reaction mixture was purified by silica gel column chromatography (0-80 percent ethyl acetate in hexanes). The resulting material was subjected to a second silica gel column (0-20 percent methanol in dichloromethane). Clean fractions were combined and concentrated to afford the title compound as a white solid (2.3O g, 11.6 mmol, 58 percent yield). MS (ESI) m/z 198.0 [M+l]+. |
42.4% | for 20 h; Reflux | 5-bromo-4-methyl-pyridine-2-carbonitrile: To a solution of 2,5-dibromo-4-methylpyridine (15 g, 59.8 mmol, Eq: 1.00) in DMF (100 ml) was added copper(I) cyanide (4.28 g, 47.8 mmol, Eq: 0.8) and sodium cyanide (2.34 g, 47.8 mmol, Eq: 0.8). The reaction mixture was refluxed for 20 hr at which point a precipitate formed. Upon cooling water was added and the mixture sonicated. The solids were filtered and washed with water. The resulting filtrate was extracted with EtOAc and the organic layers then combined, washed with water and brine, and concentrated under reduced pressure. The crude material was then purified by column chromatography (0-10percent EtOAc/Hex gradient) to give 5-bromo-4-methyl-pyridine-2-carbonitrile (5 g, 42.4percent yield) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42.4% | With copper(l) cyanide In N,N-dimethyl-formamide for 20 h; Reflux | 5-bromo-4-methyl-pyridine-2-carbonitrile:To a solution of 2,5-dibromo-4-methylpyridine (15 g, 59.8 mmol, Eq: 1.00) in DMF (100 ml) was added copper(1) cyanide (4.28 g, 47.8 mmol, Eq: 0.8) and sodium cyanide (2.34 g, 47.8 mmol, Eq: 0.8). The reaction mixture was refluxed for 20 hr at which point a precipitate formed. Upon cooling water was added and the mixture sonicated. The solids were filtered and washed with water. The resulting filtrate was extracted with EtOAc and the organic layers then combined, washed with water and brine, and concentrated under reduced pressure. The crude material was then purified by column chromatography (0-10percent EtOAc/Hex gradient) to give 5-bromo-4-methyl-pyridine-2-carbonitrile (5 g, 42.4percent yield) as a white solid. |
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