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With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 110℃; for 120h;
In 15 ml of DMF were dissolved 500 mg OFTETRAFLUORONITRILE (2.5 mmol), 7 g of CYCLOHEXYLMETHANOL (62 mmol) and 8.6 g of potassium carbonate (62MMOL). The mixture was heated to 110 oC for 5 days. After this period, the reaction mixture was poured into 200 ml of water and extracted with 3 x 50 ml of ether. The combined ether layers were washed with 100 ml of water followed by 100 ml of brine. After drying over sodium sulfate, the solvent was removed and the remaining oily material purified by flash silica gel chromatography using a mixture of dichloromethane : methanol = 20: 1 as the eluting solvent. The first fraction was collected and the solvent was evaporated. The resulting yellow solid (1 g, yield: 70percent), which had a melting point of 70-72 oC, was confirmed to be the desired product BY IH NMR spectroscopy, IR spectroscopy and EI-MS (M+ = 576.39).
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20℃; for 5h;
General procedure: 2.5mmol thiazole-4-carboxyli acid and 2.0mmol alcohol were dissolved in 25mL dichloromethane (DCM) in a dry flask with continuous stirring, followed by the addition of 2.5mmol 3-(3-dimethylaminopropyl) -1-ethylcarbodiimide hydrochloride. When the temperature of the reaction system cooled to 0°C, 0.2mmol 4-dimethylaminopyridine was added dropwise and reacted for 1hat 0°C. Then the temperature was elevated to room temperature for another 4h reaction. The reaction was stopped by adding 25mL saturated NaHCO3 solution and extracted twice with 20mL dichloromethane (2×20mL). The extracted organic layers were first dried by anhydrous Na2SO4, and then filtered and concentrated under vacuum distillation, obtaining the crude products. Finally, the crude products were further purified using column chromatography (ethy lacetate:petroleum ether, 1:5).
1-chloro-2-(cyclohexylmethoxy)-3-nitrobenzene[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
15 g
With caesium carbonate; In N,N-dimethyl-formamide; at 50℃; for 12h;
[00737] To a solution of <strong>[2106-49-2]1-chloro-2-fluoro-3-nitrobenzene</strong> (10 g, 56.8 mmol) in DMF (50 mL) was added cyclohexylmethanol (9.7 g, 30 mmol) followed by Cs2CO3 (42.5 g, 130.6 mmol) , then stirred at 50 OC for 12 h. The reaction was diluted with water, extracted with EtOAC, purified by SGC (eluting with 0-5% EtOAc in PE) to afford 1-chloro-2-(cyclohexylmethoxy)-3-nitrobenzene (15 g) as a yellow oil. MS (EI+, m/z): 292.0[M+Na]+.
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