2-broMo-5-(difluoroMethoxy)pyridine

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2-broMo-5-(difluoroMethoxy)pyridine Basic information
Product Name:2-broMo-5-(difluoroMethoxy)pyridine
Synonyms:2-broMo-5-(difluoroMethoxy)pyridine;Pyridine,2-bromo-5-(difluoromethoxy)-;2-Bromo-5-(difluoromethoxy)
CAS:845827-14-7
MF:C6H4BrF2NO
MW:224
EINECS:
Product Categories:
Mol File:845827-14-7.mol
2-broMo-5-(difluoroMethoxy)pyridine Structure
2-broMo-5-(difluoroMethoxy)pyridine Chemical Properties
Boiling point 235.2±35.0 °C(Predicted)
density 1.670±0.06 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
pka-3.29±0.10(Predicted)
form liquid
color Pale yellow
Safety Information
HS Code 2933399990
MSDS Information
2-broMo-5-(difluoroMethoxy)pyridine Usage And Synthesis
Synthesis
2-Bromo-5-hydroxypyridine

55717-45-8

Sodium chlorodifluoroacetate

1895-39-2

2-broMo-5-(difluoroMethoxy)pyridine

845827-14-7

Using 6-bromopyridin-3-ol (1.2 g, 6.9 mmol) and sodium difluorochloroacetate (2.1 g, 13.8 mmol) as raw materials, potassium carbonate (1.24 g, 8.97 mmol) was added in anhydrous DMF (10 ml) and the mixture was stirred and reacted for 20 hrs at 80 °C. After completion of the reaction, it was cooled to room temperature and the reaction mixture was partitioned between EtOAc and water. The aqueous layer was back-extracted with EtOAc, the organic phases were combined, dried over anhydrous sodium sulfate and concentrated. The crude product was purified by chromatography on a Redi-Sep pre-populated silica gel column (40 g) using a gradient elution with hexane solution from 0 to 10% EtOAc to afford 2-bromo-5-difluoromethoxypyridine (0.89 g, 4.0 mmol, 58% yield) as a colorless oil.ESI-MS (M+1) m/z: 225.8.

References[1] Journal of Medicinal Chemistry, 2010, vol. 53, # 23, p. 8421 - 8439
[2] Patent: US2013/225552, 2013, A1. Location in patent: Paragraph 0902
[3] Patent: EP1741703, 2007, A1. Location in patent: Page/Page column 73
[4] Patent: US2018/37594, 2018, A1. Location in patent: Paragraph 0280-0283
[5] Patent: US2014/249104, 2014, A1. Location in patent: Page/Page column
2-broMo-5-(difluoroMethoxy)pyridine Preparation Products And Raw materials
Raw materials2-Bromo-5-hydroxypyridine-->Sodium chlorodifluoroacetate-->N,N-Dimethylformamide-->Potassium carbonate
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