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Chemical Structure| 1201924-34-6 Chemical Structure| 1201924-34-6

Structure of 1201924-34-6

Chemical Structure| 1201924-34-6

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Product Details of [ 1201924-34-6 ]

CAS No. :1201924-34-6
Formula : C8H7BrClNO2
M.W : 264.50
SMILES Code : O=C(OC)C1=NC(Cl)=CC=C1CBr
MDL No. :MFCD18251164

Safety of [ 1201924-34-6 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H335-H314
Precautionary Statements:P260-P264-P270-P271-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P403+P233-P405-P501
Class:8
UN#:3261
Packing Group:

Application In Synthesis of [ 1201924-34-6 ]

* 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 [ 1201924-34-6 ]

[ 1201924-34-6 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 878207-92-2 ]
  • [ 1201924-34-6 ]
YieldReaction ConditionsOperation in experiment
68% With N-Bromosuccinimide; acetic acid; dibenzoyl peroxide; In tetrachloromethane; at 100℃; for 1h; [00486] To a flask containing a magnetic stir bar was added methyl 6-chloro-3- methylpicolinate (750 mg, 4.04 mmol, 1.0 eq.), followed by CC (15.0 mL). To this mixture was added N-bromosuccinimide (1.44 g, 8.08 mmol, 2.0 eq.), benzoyl peroxide (29.4 mg, 0.12 mmol, 0.03 eq.), and acetic acid (231 mu, 4.04 mmol, 1.0 eq.). The reaction mixture was stirred at 100 C for 1 hour. The reaction mixture was cooled to room temperature and quenched with saturated aquesous NH4.CI solution (10 mL). The mixture was extracted with CH2CI2 (3x). The organic layers were combined, dried over Na2SC>4, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel to provide the desired compound as a solid (735 mg, 68%). ES-MS [M+l]+: 265.8.
65% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 80℃; A solution of 6-chloro-3-methylpicolinate (100 mg, 0.58 mmol), NBS (104 mg, 0.58 mmol) and AIBN (2 mg, 11 muiotaetaomicron) in CC14 (10 mL) was stirred at 80C overnight. After reaction, the mixture was concentrated and the residue was purified by prep-TLC (PE : EtOAc = 5 : 1) to give the product of methyl 3-(bromomethyl)-6-chloropicolinate (100 mg, yield: 65%). XH-NMR (CDCI3, 400 MHz) delta 7.85 (d, J= 8.0 Hz, 1H), 7.49 (d, J= 8.0 Hz, 1H), 4.81 (s, 2H), 4.01 (s, 3H). MS (M+H)+: 264 / 266 / 268.
65% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 80℃; A solution of 6-chloro-3-methylpicolinate (100 mg, 0.58 mmol), NBS (104 mg, 0.58 mmol) and AIBN (2 mg, 11 imol) in CC14 (10 mL) was stirred at 80C overnight. After reaction,the mixture was concentrated and the residue was purified by prep-TLC (PE : EtOAc = 5 : 1) to give the product of methyl 3-(bromomethyl)-6-chloropicolinate (100 mg, yield: 65%). ?H-NMR (CDC13, 400 MHz) 7.85 (d, J= 8.0 Hz, 1H), 7.49 (d, J= 8.0 Hz, 1H), 4.81 (s, 2H), 4.01 (s, 3H). MS (M+H): 264 / 266 / 268.
64% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In 1,2-dichloro-ethane; at 85℃; for 72h;Inert atmosphere; <strong>[878207-92-2]methyl 6-chloro-3-methylpicolinate</strong> (100 mg, 539 muiotaetaomicron, Eq: 1) and N-bromosuccinimide (95.9 mg, 539 muiotaetaomicron, Eq: 1) were dissolved in 1,2-dichloroethane (1.1 ml) under argon atmosphere. Azobisisobutyronitrile (8.85 mg, 53.9 muiotaetaomicron, Eq: 0.1) was then added. The reaction mixture was stirred at 85 C for 3 days, after 2 more additions of N-bromosuccinimide and azobisisobutyronitrile. The reaction mixture was concentrated in vacuo. The residue was purified by chromatography on silica gel to afford the desired product as a white solid (92 mg, 64 %). MS (m/z) = 266.0 [M + H]+.
59% With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 3h;Reflux; A carbon tetrachloride (10 ml) solution of 6-chloro-3-methyl methyl picolinate (500 mg, 2.69 mmol), N-bromosuccinimide (719 mg, 4.04 mmol), and benzoyl peroxide (124 mg, 0.23 mmol) was refluxed for 3 h. After completion of reaction, the reaction mixture was evaporated under reduced pressure and the resulting residue was purified by silica gel column chromatography (2% EA/Hexnae) to give 422 mg (yield 59%) of the title compound. 1H NMR(300 MHz, CDCl3) delta 8.50 (d, J = 8.2 Hz, 1H), 7.49 (d, J = 8.2 Hz, 1H), 4.89 (s, 2H), 4.02 (s, 3H).
37% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 80℃; for 16h;Inert atmosphere; To a solution of <strong>[878207-92-2]methyl 6-chloro-3-methyl-pyridine-2-carboxylate</strong> (5.0 g, 26.94 mmol) and 1- bromo-2,5-pyrrolidinedione (4.8 g, 26.94 mmol) in carbon tetrachloride (10 ml) under nitrogen atmosphere was added azobisisobutyronitrile (0.44 g, 2.69 mmol). The mixture was stirred at 80 C for 16h, diluted with water (50 ml) and extracted with ethyl acetate (100 ml x 3). The combined organic phases were washed with brine (100 ml x 2), dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel column (0381) chromatography (eluent: 20% ethyl acetate: petroleum ether) to afford methyl 3- (bromomethyl)-6-chloro-pyridine-2-carboxylate (5.3 g, 37%) as a white solid. 1H NMR (400 MHz, CDC13): delta 7.86 (d, / = 8.0 Hz, 1H), 7.50 (d, / = 8.0 Hz, 1H), 4.89 (s, 2H), 4.03 (s, 3H).
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 6h;Reflux; Step 5. Methyl 3 -(bromomethyl)-6-chloropyridine-2-carboxylateMethyl 6-chloro-3-methylpyridine-2-carboxylate (3.46 g, 18.6 mmol), NBS (3.32 g, 18.6 mmol) and AIBN (61 mg, 0.37 mmol) were stirred in refluxing CCl4 (40 mL) for 6 hours. The mixture was then cooled to room temperature and purified directly by silica gel chromatography (2-20% EtOAc/hexanes) to give the title compound as a white solid. LRMS (APCI) calc'd for (C8H8BrClNO2) [M+Hf, 266; found 266.

  • 2
  • [ 1201924-31-3 ]
  • [ 1201924-34-6 ]
 

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