2-Fluoro-5-bromoanisole Chemical Properties

Boiling point:

205.8±20.0 °C(Predicted)

Density 

1.531±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

Liquid

Appearance

Colorless to off-white Liquid

InChIKey

SEVMQEIGENUPIE-UHFFFAOYSA-N

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36-52

Safety Statements 

26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2909309090

2-Fluoro-5-bromoanisole Usage And Synthesis

Chemical Properties

Pale yellow liquid

Uses

5-Bromo-2-fluoroanisole is a reactant used in the preparation of bicyclic substituted hydroxyphenylmethanone derivatives as 17β-hydroxysteroid dehydrogenase type 2 (17β-HSD2) inhibitors for the treatment of osteoporosis.

Synthesis

5-Bromo-2-fluorophenol (13.0 g, 68.1 mmol) and iodomethane (19.3 g, 136 mmol) were dissolved in DMF (120 mL) and potassium carbonate (18.8 g, 136 mmol) was added. The reaction mixture was stirred at room temperature for 65 hours. After completion of the reaction, water (150 mL) was added to the reaction solution and extracted with ethyl acetate (100 mL x 1,50 mL x 2). The organic layers were combined, dried with anhydrous magnesium sulfate and concentrated under reduced pressure to give a light yellow oily crude product (29.0 g). The crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=10:1) to afford 5-bromo-2-fluoroanisole (14.2 g, yield: quantitative) in colorless oily form. The structure of the product was confirmed by 1H-NMR (400 MHz, CDCl3) and 19F-NMR (376 MHz, CDCl3): 1H-NMR δ 3.88 (s, 3H), 6.95 (dd, J = 8.6 and 10.8 Hz, 1H), 7.02 (ddd, J = 2.2,4.2 and 8.6 Hz, 1H), 7.08 (dd. J = 2.2 and 7.6 Hz, 1H); 19F-NMR δ -137 (s, 1F).

References

[1] Patent: US2016/24110, 2016, A1. Location in patent: Paragraph 0452; 0453
[2] Patent: WO2006/76246, 2006, A2. Location in patent: Page/Page column 87
[3] Patent: US2010/227894, 2010, A1. Location in patent: Page/Page column 28
[4] Patent: US2007/3539, 2007, A1. Location in patent: Page/Page column 71

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