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Chemistry
Heterocyclic Building Blocks
Pyridines
3-bromo-5-chloropyridine
2-(5-Bromo-3-chloropyridin-2-yl)acetonitrile
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
Pyridines
Bromides Chlorides Nitriles
3-bromo-5-chloropyridine

[ CAS No. 1227515-31-2 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
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Chemical Structure| 1227515-31-2
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Quality Control of [ 1227515-31-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
Alternatived Products of [ 1227515-31-2 ]

Product Details of [ 1227515-31-2 ]

CAS No. :1227515-31-2 MDL No. :MFCD16608791
Formula : C7H4BrClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :SPUABSOFIGYJTJ-UHFFFAOYSA-N
M.W : 231.48 Pubchem ID :86707221
Synonyms :

Safety of [ 1227515-31-2 ]

Signal Word:Danger Class:8,6.1
Precautionary Statements:P261-P280-P301+P310-P305+P351+P338 UN#:2923
Hazard Statements:H301-H315-H317-H318-H335 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 1227515-31-2 ]

* 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.

  • Downstream synthetic route of [ 1227515-31-2 ]

[ 1227515-31-2 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 97966-00-2 ]
  • [ 75-05-8 ]
  • [ 1227515-31-2 ]
YieldReaction ConditionsOperation in experiment
23.4 g With lithium hexamethyldisilazane; In tetrahydrofuran; at 20 - 35℃; for 1h;Inert atmosphere; PREPARATION EXAMPLE 3: N-rri -(3-chloro-5-cvcloDroDyl-2-DyridvncvcloDroDyllmethyll- 2-(trifluoromethyl)benzamide (compound A.95)Step 1 : (5-Bromo-3-chloro-pyridin-2-yl)-acetonitrile 27.0 g of <strong>[97966-00-2]5-bromo-2,3-dichloropyridine</strong> was dissolved in 450 ml of anhydroustetrahydrofuran and 7.33 g of acetonitrile was added at ambient temperature under argon. 262 ml of lithium hexamethyldisilazide (1 N solution in tetrahydrofuran) was added dropwise over a period of 45 min, during which the temperature rose to 35C.Subsequently, the reaction mixture was stirred at ambient temperature for 1 h, then the reaction mixture was poured into 800 ml of cold water and was extracted with two 1 L portions of diethyl ether. The combined organic phases were washed with brine, dried over sodium sulfate, filtered and concentrated. 29.4 g of crude material was obtained as a brown oil. It was purified by chromatography on silica gel, using heptane/ethyl acetate (9:1 ) as a eluent. Thus, 23.4 g of (5-bromo-3-chloro-pyridin-2-yl)-acetonitrile was obtained as a orange oil. 1H-NMR (CDCI3): 8.60 ppm (s, 1 H), 7.92 ppm (s, 1 H), 4.00 ppm (s, 2H).
23.4 g With lithium hexamethyldisilazane; In tetrahydrofuran; at 35℃; for 1h;Inert atmosphere; 27.0 g of <strong>[97966-00-2]5-bromo-2,3-dichloropyridine</strong> was dissolved in 450 ml of anhydroustetrahydrofuran and 7.33 g of acetonitrile was added at ambient temperature under argon. 262 ml of lithium hexamethyldisilazide (1 N solution in tetrahydrofuran) was added dropwise over a period of 45 min, during which the temperature rose to 35C. Subsequently, the reaction mixture was stirred at ambient temperature for 1 h, then the reaction mixture was poured into 800 ml of cold water and was extracted with two 1 L portions of diethyl ether. The combined organic phases were washed with brine, dried over sodium sulfate, filtered and concentrated. 29.4 g of crude material was obtained as a brown oil. It was purified by chromatography on silica gel, using heptane/ethyl acetate (9:1 ) as a eluent. Thus, 23.4 g of (5-bromo-3-chloro-pyridin-2-yl)-acetonitrile was obtained as a orange oil. 1H-NMR (CDCI3): 8.60 ppm (s, 1 H), 7.92 ppm (s, 1 H), 4.00 ppm (s, 2H)
23.4 g With lithium hexamethyldisilazane; In tetrahydrofuran; at 20 - 35℃; for 1.75h;Inert atmosphere; 27.0 g of <strong>[97966-00-2]5-bromo-2,3-dichloropyridine</strong> was dissolved in 450 ml of anhydrous tetrahydrofuran and 7.33 g of acetonitrile was added at ambient temperature under argon. 262 ml of lithium hexamethyldisilazide (1 N solution in tetrahydrofuran) was added dropwise over a period of 45 min, during which the temperature rose to 35C. Subsequently, the reaction mixture was stirred at ambient temperature for 1 h, then the reaction mixture was poured into 800 ml of cold water and was extracted with two 1 L portions of diethyl ether. The combined organic phases were washed with brine, dried over sodium sulfate, filtered and concentrated. 29.4 g of crude material was obtained as a brown oil. It was purified by chromatography on silica gel, using heptane/ethyl acetate (9:1 ) as a eluent. Thus, 23.4 g of (5-bromo-3-chloro-pyridin-2-yl)-acetonitrile was obtained as a orange oil. 1H-NMR (CDCI3): 8.60 ppm (s, 1 H), 7.92 ppm (s, 1 H), 4.00 ppm (s, 2H).
Reference： [1]Patent: WO2013/64521,2013,A1 .Location in patent: Page/Page column 97; 98
[2]Patent: WO2013/64519,2013,A1 .Location in patent: Page/Page column 79
[3]Patent: WO2014/173921,2014,A1 .Location in patent: Page/Page column 52
  • 2
  • [ 97966-00-2 ]
  • [ 105-56-6 ]
  • [ 1227515-31-2 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; In 1-methyl-pyrrolidin-2-one; at 0 - 70℃; for 3h; To a solution of <strong>[97966-00-2]5-bromo-2,3-dichloropyridine</strong> (10.0 g, 0.044 mol) in N-methyl- 2-pyrrolidone (70 mL) at 0 C was added potassium hydroxide (5.4 g, 0.097 mol), and the resulting mixture was heated to 70 C. Ethyl cyanoacetate (5.65 mL, 0.53 mol) was added via syringe over 15 min, and then heating at 70 C was continued for 3 h more. The pH of the reaction mixture was adjusted to 2 by careful addition of concentrated aqueous hydrochloric acid, and the resulting mixture was heated at 130 C for 2 h. The reaction mixture was cooled to 20 C, treated with 1 N aqueous sodium hydroxide (15-16 mL) and extracted with three portions of methyl tert-butyl ether (3 x 100 mL). The combined organic extracts were washed with water, dried (Na2SO4) and concentrated under reduced pressure to afford the title compound (6.0 g) as a brown colored solid, which was used without further purification. H NMR delta 8.60 (s, 1H), 7.79 (s, 1H), 4.01 (s, 2H).
Reference： [1]Patent: WO2014/4064,2014,A1 .Location in patent: Page/Page column 39
  • 3
  • [ 97966-00-2 ]
  • [ 1227515-31-2 ]
Reference： [1]Patent: WO2015/28427,2015,A1
[2]Patent: WO2015/55535,2015,A1
[3]Patent: WO2015/91424,2015,A1

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