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CAS No. : | 22445-42-7 | MDL No. : | MFCD00060670 |
Formula : | C9H9N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YFKRLZLGVDDKAL-UHFFFAOYSA-N |
M.W : | 131.17 | Pubchem ID : | 89718 |
Synonyms : |
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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: |
* 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 |
---|---|---|
81% | With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 3h;Heating / reflux; UV-irradiation; | 3-(bromomethyl)-5-methylbenzonitrile; To a stirred solution of carbon tetrachloride (270 mL), was added <strong>[22445-42-7]3,5-dimethylbenzonitrile</strong> (37 g, 0.282M), N-bromo succinimide (NBS) (50 g, 0.282 M), and benzoyl peroxide (3.4 g, 14 mmol). The mixture was then refluxed for 3 hr. under a light of 500 W tungsten lamp. After cooling to room temperature, the mixture was filtered, evaporated, and the residue was purified by silica gel column chromatography (eluent, ether:hexane (1:10)) to give 48 g (81%) of 3-(bromomethyl)-5-methylbenzonitrile as a white solid. m.p. 80-81 C. 1H NMR (200 MHz, CDCl3) delta 2.39(3H, s), 4.43 (2H, s), 7.39 (1H, s), 7.43 (1H, s), 7.48 (1H, s). |
48% | With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 3h;Heating / reflux; UV-irradiation; | To a solution of 3,5- dimethylbenzonitrile (25 g, 190 mmol) in carbon tetrachloride (190 mL) was added N-bromosuccinimide (33.9 g, 190 mmol) and benzoyl peroxide (2.28 g, 9.4 mmol). The reaction mixture was refluxed under a UV lamp for 3 h, cooled to room temperature and filtered. The filtrate was concentrated and purified by silica gel chromatography (10% ethyl ether/ hexanes) to give an impure product. The product was crystallized from refluxing ethyl ether (100 mL) and hexanes (400 mL) to give a white solid (19.11 g, 48%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With thionyl chloride;N,N-dimethyl-formamide; In benzene; for 2h;Heating / reflux; | 3,5-dimethylbenzonitrile; 3,5-dimethylbenzamide (50 g, 0.3356M) was suspended in benzene (400 mL). Thionyl chloride (49 mL, 0.671M) and DMF (2 mL) were added and the mixture was refluxed for 2 hr. After cooling to room temperature, the mixture was poured into a crushed ice. After 1 hr., the solution was neutralized by the addition of 6N sodium hydroxide solution. The product was then extracted with ether, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo to give a yellow solid. The crude product was then purified by silica gel column chromatography (eluent, EA:hexane (1:4)) to afford 42 g (95%) of 3,5-dimethylbenzonitrile as a yellow solid. m.p. 51-52 C. 1H NMR (300 MHz, CDCl3) delta 2.34(6H, s), 7.21 (1H, s), 7.26 (2H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In 1,2-dichloro-ethane; at 80℃; for 9h;Inert atmosphere; | 3,5-Bis(bromomethyl)benzonitrile To a solution of <strong>[22445-42-7]3,5-dimethylbenzonitrile</strong> (1.00 g, 7.62 mmol, 1 euiv.) in 1 ,2-dichloroethane (76 ml_), were added A/-bromosuccinimide (2.98 g, 16.8 mmol, 2.2 equiv.) and azobisisobutyronitrile (0.250 g, 1.52 mmol, 0.2 equiv.). The reaction mixture was stirred under an argon atmosphere for 9 h at 80 C. H20 was added to the medium which was extracted three times with CH2CI2. The combined organic layers were washed with brine, dried over Na2S04 and concentrated under reduced pressure. The residue was purified by flash chromatography (25 g BioTage HP Sil cartridge, 2% to 15% EtOAc/Hexane gradient, 20 CV) to yield 3,5-bis(bromomethyl)benzonitrile (0.618 g, 28%) as white crystals. Similar data as described in literature. NMR (CDCI3, 500 MHz) delta 7.64 (s, 1 H), 7.61 (d, 2H, J= 1.2 Hz), 4.45 (s, 4H); HPLC purity: 99%, tR = 2.9 min (Method 1 ). Similar data as described in literature (Easson, M. W.; Fronczek, F. R.; Jensen, T.; Vicente, M. G. H. Bioorg. Med. Chem. 2008, 16, 3191 -3208). |