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CAS No. : | 1033463-31-8 | MDL No. : | MFCD11100207 |
Formula : | C7H5ClF3NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GJPVRQMKHNSMCO-UHFFFAOYSA-N |
M.W : | 211.57 | Pubchem ID : | 27282725 |
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: |
* 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 |
---|---|---|
With triethylamine In dichloromethane at 0 - 25℃; | 5.1 To a 10 ml vial were added t3-chloro-5-(trifluoromethyl)pyridin-2-yl]methanol (0.30 g, 1.42 mmol), TEA (0.59 ml, 4.3 mmol) and 5 ml dichloromethane. Methanesulfonyl chloride was added at 0 °C. The resulting reaction mixture was stirred at room temperature for 20 minutes. It was diluted with 20 ml EtOAc, washed with 30 ml water. Organics were dried over sodium sulfate, filtered and concentrated. Residue was purified on silica gel column eluted with 4:1 EtOAc/hexane to give 0.38 g title compound.1H-NMR (CDCl3): δ: 8.84 (s, IH), 8.03 (s, IH), 5.55 (s, 2H), 3.20 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With methanol; sodium tetrahydridoborate at 0 - 23℃; for 4h; | 2 Step 2: (3-chloro-5-(trifluoromethyl)pvridin-2-yl)methanol NaBH4 (12g, 31 .6mmol) was added portion wise to a stirred solution of ethyl 3-chloro-5-(trifluoromethyl)- picolinate (40g, 15.8mmol) in MeOH (200ml) at 0°C and stirred for4 h at RT. The RM was slowly quenched with water (500mL) and the organic product was extracted with EtOAc (3x200mL). The organiclayer was washed with brine (300mL), then dried over anhydr. Na2SO4, filtered and evaporated the solvent under vacuo to give crude product. The crude was purified by CC (0-15% EtOAc in PE) and the pure fractions were concentrated at below 40°C to give (3-chloro-5-(trifluoromethyl)pyridin-2-yl)methanol (20g, 60%), as a thick liquid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With Dess-Martin periodane In dichloromethane at 0 - 23℃; for 3h; | 3 Step 3: (3-chloro-5-(trifluoromethyl)pyridin-2-yl)methanol DMP (60.2g, 142.lommol) was added portion wise to a stirred solution of(3-chloro-5-(trifluoromethyl)- pyridin-2-yl)methanol (15g, 71.Ommol) in DCM (lOOmL) at 0°C and stirred for 3 h at RT. The RM was filtered through a celite bed and washed with DCM (3x1 OOmL).The clear filtrate was washed with aq. NaHCO3 (200mL), water (200mL), brine(250mL), dried over anhydr. Na2SO4, filtered, concentrated under reduced pressure to get the crude product. The crude was purified by CC (0-5% EtOAc in PE) to give (3-chloro-5-(trifluoromethyl)pyridin-2-yl)methanol (8g, 57%) as liquid.. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C 2: dichloromethane / 40 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C 2: dichloromethane / 40 °C 3: Cs2CO3 / acetonitrile / 40 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C 2: dichloromethane / 40 °C 3: Cs2CO3 / acetonitrile / 40 °C / Inert atmosphere 4: potassium peroxomonosulfate / acetonitrile; lithium hydroxide monohydrate / 23 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C 2.1: dichloromethane / 40 °C 3.1: Cs2CO3 / acetonitrile / 40 °C / Inert atmosphere 4.1: potassium peroxomonosulfate / acetonitrile; lithium hydroxide monohydrate / 23 °C 5.1: lithium aluminium hydride / tetrahydrofuran / 0.25 h / -78 °C 5.2: 23 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C 2.1: dichloromethane / 40 °C 3.1: Cs2CO3 / acetonitrile / 40 °C / Inert atmosphere 4.1: potassium peroxomonosulfate / acetonitrile; lithium hydroxide monohydrate / 23 °C 5.1: lithium aluminium hydride / tetrahydrofuran / 0.25 h / -78 °C 5.2: 23 °C 6.1: pyridine / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C 2.1: dichloromethane / 40 °C 3.1: Cs2CO3 / acetonitrile / 40 °C / Inert atmosphere 4.1: potassium peroxomonosulfate / acetonitrile; lithium hydroxide monohydrate / 23 °C 5.1: lithium aluminium hydride / tetrahydrofuran / 0.25 h / -78 °C 5.2: 23 °C 6.1: pyridine / 60 °C 7.1: potassium peroxomonosulfate / acetonitrile; tetrahydrofuran; lithium hydroxide monohydrate / 40 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C 2.1: dichloromethane / 40 °C 3.1: Cs2CO3 / acetonitrile / 40 °C / Inert atmosphere 4.1: potassium peroxomonosulfate / acetonitrile; lithium hydroxide monohydrate / 23 °C 5.1: lithium aluminium hydride / tetrahydrofuran / 0.25 h / -78 °C 5.2: 23 °C 6.1: pyridine / 60 °C 7.1: potassium peroxomonosulfate / acetonitrile; tetrahydrofuran; lithium hydroxide monohydrate / 40 °C 8.1: chiral-LC IC-column / ethanol; n-heptane / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: palladium diacetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; anhydrous Sodium acetate / 6 h / 90 °C / 11377.6 Torr / Autoclave 2: methanol; sodium tetrahydridoborate / 4 h / 0 - 23 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89.2% | With phosphorus tribromide In dichloromethane at 20℃; for 4.5h; Cooling with ice; | 1 Synthesis of 3-chloro-5-trifluoromethyl-2-bromomethylpyridine A three-neck reaction flask equipped with a motor and a dropping funnel was charged with 21.1 g (0.1 mol) of 3-chloro-5-trifluoromethyl-2-Pyridine methanol and 70 mL of methylene chloride. 54.1 g (0.2 mol) of phosphorus tribromide was added dropwise with stirring in an ice bath and the temperature was raised to room temperature for 4.5 h. After the reaction of the starting material was completed, the mixture was slowly poured into 300 mL of saturated sodium bicarbonate solution , The mixture was extracted with 80 mL of ethyl acetate four times, the combined organic layer was washed twice with 200 mL of saturated brine, dried over anhydrous sodium sulfate, the solvent was removed to remove ethyl acetate, the intermediate 3-chloro-5- Trifluoromethyl-2-bromomethylpyridine 24.5 g, content 96.3%, yield 89.2%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.43% | With sulfuric acid In toluene at 100℃; | 3 Example 3 (1) Add 21.18 (0.111101) 2-hydroxymethyl-3-chloro-5-trifluoromethylpyridine to the reaction flask.37.88 (0.2mol) 2,6-dichlorobenzonitrile and 276 · 4g (3 · Omol) toluene were cooled down to -20°C,Then add 25 · 0g (0 • 25 mol) dropwise98% concentrated sulfuric acid,After heating up, it warms up to 100 °C.In HPLC, the weight content of 2-hydroxymethyl-3-chloro-5-trifluoromethylpyridine is less than 0.5%.Reaction solution, (2) Cool the reaction solution to 0°C and add 100.0g (0.25mol) of 10% NaOH in water.The reaction liquid is neutralized in a liquid and then filtered to obtain a solid, and the solid is washed with water and dried; (3) Add the solid obtained in step (2) to a mixture of 32 · 4g (1 · 8mol) water and 41 · 4g (0 · 9mol) ethanolIn the middle, 1.0 hr after dispersion, the solid was filtered, and the solid was washed with water and dried to obtain 34.6 g of 2,6-dichloro-N-[ (3-Chloro-5-difluoromethyl-2-R (pyridinium) methyl] benzamide is the finished product carbendazim, with a yield of 90.43% and a purity of 97.51%. |
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