3-FLUORO-5-METHOXY-PHENOL Chemical Properties

Boiling point:

222.0±20.0 °C(Predicted)

Density 

1.224±0.06 g/cm3(Predicted)

storage temp. 

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

pka

8.59±0.10(Predicted)

Appearance

White to off-white Solid

Safety Information

HS Code 

2909500090

3-FLUORO-5-METHOXY-PHENOL Usage And Synthesis

Uses

3-Fluoro-5-methoxyphenol is a useful research chemical used in the preparation of tetracyclicindole derivatives for hepatitis c treatment as well as biaryl ethers as reverse transcriptase inhibitors.

Synthesis

Example 50: Synthesis of 3-{5-[(6-amino-1H-pyrazolo[3,4-b]pyridin-3-yl)methoxy]-2-chloro-3-fluorophenoxy}-5-chlorobenzenecarbonitrile; Step 1: Preparation of 3-fluoro-5-methoxyphenol (50-1); Under nitrogen protection, 1-fluoro-3,5-dimethoxybenzene (25 g, 160 mmol) was dissolved in dichloromethane ( 200 mL, 0.8 M) and subsequently cooled to -15 °C. Boron tribromide (176 mL, 176 mmol, 1 M solution in dichloromethane) was added slowly. The reaction mixture was stirred at -15 °C for 1.5 h, followed by stirring at room temperature for 10 min. The reaction mixture was cooled again to 0 °C and the reaction was quenched by slowly adding water (150 mL). The aqueous layer was extracted with dichloromethane (3 x 100 mL). The organic layers were combined, dried over sodium sulfate and concentrated. Purification by silica gel column chromatography (1%-30% ethyl acetate/hexane) afforded the mono-demethylated product 3-fluoro-5-methoxyphenol (50-1) (15 g, 67% yield).

References

[1] Journal of Medicinal Chemistry, 2009, vol. 52, # 22, p. 7163 - 7169
[2] Patent: US2007/21442, 2007, A1. Location in patent: Page/Page column 57-58
[3] Patent: WO2007/34325, 2007, A1. Location in patent: Page/Page column 48
[4] Patent: WO2005/37763, 2005, A1. Location in patent: Page/Page column 94-95
[5] Patent: US2015/191473, 2015, A1. Location in patent: Paragraph 0173

3-FLUORO-5-METHOXY-PHENOL(850793-25-8)Related Product Information

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