5-Bromo-2-hydroxy-3-(trifluoromethyl)pyridine Chemical Properties

Boiling point:

229.4±40.0 °C(Predicted)

Density 

1.876±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

7.61±0.10(Predicted)

form 

Solid

Appearance

White to light brown Solid

InChI

InChI=1S/C6H3BrF3NO/c7-3-1-4(6(8,9)10)5(12)11-2-3/h1-2H,(H,11,12)

InChIKey

OPLCXLXORZDTMX-UHFFFAOYSA-N

SMILES

C1(=O)NC=C(Br)C=C1C(F)(F)F

CAS DataBase Reference

76041-79-7

Safety Information

HS Code 

2933399990

5-Bromo-2-hydroxy-3-(trifluoromethyl)pyridine Usage And Synthesis

Synthesis

Step 1: 3-(Trifluoromethyl)pyridin-2(1H)-one (25.0 g, 0.15 mol) was dissolved in acetic acid (300 mL) and sodium acetate (15.1 g, 0.18 mol) and bromine (8.6 mL, 0.17 mol) were added sequentially, dropwise. The reaction mixture was stirred at 80°C overnight. After completion of the reaction, the mixture was concentrated, diluted with saturated aqueous sodium bicarbonate and extracted twice with ethyl acetate. The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. Purification by column chromatography (petroleum ether/ethyl acetate = 7/2) afforded the target compound 5-bromo-3-(trifluoromethyl)pyridin-2(1H)-one (P45a) (29.7 g, 80% yield) as a white solid.

References

[1] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 16, p. 6106 - 6122
[2] Patent: WO2012/139775, 2012, A1. Location in patent: Page/Page column 69-70
[3] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 23, p. 6578 - 6581
[4] Patent: US2013/12491, 2013, A1. Location in patent: Paragraph 0171; 0172

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