ChemicalBook CAS DataBase List 2-Bromo-4-methylpyridine-3-carbonitrile

2-Bromo-4-methylpyridine-3-carbonitrile synthesis

4synthesis methods

Product Name:2-Bromo-4-methylpyridine-3-carbonitrile
CAS Number:65996-02-3
Molecular formula:C7H5BrN2
Molecular Weight:197.03

Propanedinitrile, 2-[3-(dimethylamino)-1-methyl-2-propen-1-ylidene]-

71493-72-6
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65996-02-3
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Yield:65996-02-3 95%

Reaction Conditions:

with hydrogen bromide in acetic acid at 55; for 0.75 h;Flow reactor;

Steps:

Procedure:

Both columns and the coil were preheated or precooled to the appropriate temperature prior to use. The flow rates for pumps A, B, and C were set to 2.00, 0.250, and 0.250 mL/min respectively for a 4 min residence time in the heated coil. After the equilibration period, determined using the FlowCommander software, 6 × 18 mL samples were collected. Immediately after collection, 2 × 15 mL of the reaction mixture from 2 vials were charged to a mixture of AcOH (7.2 mL) and a 33 wt% HBr in AcOH solution (13.2 mL) in a round-bottom flask via syringe while stirring vigorously (three reactions from one reactor run were performed in total). A condenser was attached to the flask and the reaction was heated to 55 C for 45 min. Upon cooling the reaction to room temperature, DCM was removed in vacuo. 200 mL of water was added to the remaining solution to cause the product to precipitate out. The solution was cooled before the product was collected by vacuum filtration and dried under high vacuum over P₂O₅ to yield 6b as an orange solid (first two fractions: 1.61 g, 68%, second two fractions: 1.65 g, 70%, third two fractions fraction: 1.62 g, 69%). To remove the orange color, the product was passed through a silica plug using DCM as the eluent. Upon removal of the solvent in vacuo, 95% of 6b was recovered as an off-white solid.

References:

Longstreet, Ashley R.;Opalka, Suzanne M.;Campbell, Brian S.;Gupton, B. Frank;McQuade, D. Tyler [Beilstein Journal of Organic Chemistry,2013,vol. 9,p. 2570 - 2578] Location in patent:supporting information

93271-59-1 Synthesis

2-Hydroxy-4-methylpyridine-3-carbonitrile

93271-59-1
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65996-02-3
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References

13166-10-4
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$18.00/5g

65996-02-3
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References

3-Pyridinecarbonitrile,2-methoxy-4-methyl-(9CI)

149379-71-5
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65996-02-3
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References