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CAS No. : | 749875-16-9 | MDL No. : | MFCD10687236 |
Formula : | C7H3BrF3NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XNVAVQMVAYUTBA-UHFFFAOYSA-N |
M.W : | 270.00 | Pubchem ID : | 28306936 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
82% | Stage #1: With oxalyl dichloride In dichloromethane at 20℃; for 2 h; Stage #2: With ammonia In water; acetonitrile at 0℃; for 0.333333 h; |
To a 500 mL round bottom flask equipped with a stir bar, condenser and nitrogen inlet was charged 38.9 g (144 mmol) of δ-bromo^-trifluoromethyl-isonicotinic acid. To the solid was charged 250 mL of anhydrous dichloromethane followed by 13.2 mL (151 mmol, 1.05 eq) oxalyl chloride. To the mixture was added 0.5 mL of anhydrous dimethylformamide and the mixture was stirred at ambient temperature for 2h. The reaction was complete as evidenced by HPLC (methanol quench of aliquot). The solvent was removed in vacuo affording an amber oil.To a 1 L Erlenmeyer flask equipped with a stir bar in an ice-bath was charged 500 mL of aqueous ammonium hydroxide. To the chilled solution was added dropwise the crude acid chloride. The residue was transferred with a small amount of acetonitrile. The mixture was stirred for 20 minutes following addition. The resulting precipitate was collected by filtration and washed with water. The filter cake was dried <n="46"/>in vacuo at 45 0C affording 31.8 g of δ-bromo^-trifluoromethyl-isonicotinamide as an off-white solid in a 82percent yield. The compound may also be purified using an ether slurry and collecting the solid. |
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