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Product Details of 2,6-Dichloropyridin-3-ylboronic acid

CAS No. :148493-34-9
Formula : C5H4BCl2NO2
M.W : 191.81
SMILES Code : C1=C(N=C(C(=C1)B(O)O)Cl)Cl
MDL No. :MFCD03094989
InChI Key :XBBLBQZAVMHEER-UHFFFAOYSA-N
Pubchem ID :2762712

Safety of 2,6-Dichloropyridin-3-ylboronic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 2,6-Dichloropyridin-3-ylboronic acid

* 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.

  • Upstream synthesis route of [ 148493-34-9 ]
  • Downstream synthetic route of [ 148493-34-9 ]

[ 148493-34-9 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 148493-34-9 ]
  • [ 52764-11-1 ]
YieldReaction ConditionsOperation in experiment
91.4% With dihydrogen peroxide In dichloromethane; water at 0 - 20℃; for 0.15 h; Preparation of Compound 1Step 1 - Synthesis of 2,6-dichloropyridin-3-olΗ202 (1.60 g, 47.12 mmol) was added slowly to the solution of compound 2,6- dichloropyridin-3-ylboronic acid (3 g, 15.71 mmol) in CH2CI2 (30 mL) at 0 °C. After stirred at room temperature for about 15 hours, the mixture was quenched with sat. Na2S203 aqueous (50 mL) and adjusted to pH < 7 with IN HC1. The mixture was extracted with EtOAc (40 mL x 3). The organic layer was washed with brine (100 mL), dried over Na2S04, filtered and the solvent was evaporated to provide2,6-dichloropyridin-3-ol (2.34 g, yield: 91.4percent). 1H-NMR (CDC13, 400 MHz) δ 7.30 (d, / = 8.4 Hz, 1H), 7.19 (d, / = 8.4 Hz, 1H), 5.70 (br, 1H).
91.4% With dihydrogen peroxide In dichloromethane at 0 - 20℃; for 15 h; H202 (1.60 g, 47.12 mmol) was added slowly to the solution of compound 2,6- dichloropyridin-3-ylboronic acid (3 g, 15.71 mmol) in CH2C12 (30 mL) at 0 °C. After stirred at room temperature for about 15 hours, the mixture was quenched with sat. Na2S203 aqueous (50 mL) and adjusted to pH < 7 with IN HC1. The mixture was extracted with EtOAc (40 mL x 3). The organic layer was washed with brine (100 mL), dried over Na2S04, filtered and the solvent was concentrated in vacuo to provide 2,6-dichloropyridin-3-ol (2.34 g, yield: 91.4percent). 1H- MR (CDC13, 400 MHz) δ 7.30 (d, J= 8.4 Hz, 1H), 7.19 (d, J= 8.4 Hz, 1H), 5.70 (br, 1H). MS (M+H)+: 164 / 166 / 168.
91.4% With dihydrogen peroxide In dichloromethane at 0 - 20℃; for 15 h; Step 1-Synthesis of 2,6-dichloropyridin-3-ol
H2O2 (1.60 g, 47.12 mmol) was added slowly to the solution of compound 2,6-dichloropyridin-3-ylboronic acid (3 g, 15.71 mmol) in CH2Cl2 (30 mL) at 0° C.
After stirred at room temperature for about 15 hours, the mixture was quenched with sat. Na2S2O3 aqueous (50 mL) and adjusted to pH<7 with 1N HCl.
The mixture was extracted with EtOAc (40 mL*3).
The organic layer was washed with brine (100 mL), dried over Na2SO4, filtered and the solvent was concentrated in vacuo to provide 2,6-dichloropyridin-3-ol (2.34 g, yield: 91.4percent).
1H-NMR (CDCl3, 400 MHz) δ 7.30 (d, J=8.4 Hz, 1H), 7.19 (d, J=8.4 Hz, 1H), 5.70 (br, 1H). MS (M+H)+: 164/166/168.
References: [1] Tetrahedron, 2005, vol. 61, # 6, p. 1417 - 1421.
[2] Patent: WO2013/33900, 2013, A1, . Location in patent: Page/Page column 27.
[3] Patent: WO2013/33971, 2013, A1, . Location in patent: Page/Page column 32-33.
[4] Patent: US2014/213571, 2014, A1, . Location in patent: Paragraph 0223.
 

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