Chemical Properties
Colorless liquid to pale yellow liquid
Uses
2-Bromo-5-fluoroanisole is a halogenated anisole compound, the chemical reactivity of which is mainly concentrated on the bromine atom on its benzene ring. It can be used as an organic synthesis intermediate and a synthetic raw material for drug molecules. For example, literature reports that the substance can be used for the preparation of the drug molecule anacetrapib.
Synthesis
a) A suspension of 2-bromo-5-fluorophenol (20.0 g, 104.7 mmol) and potassium carbonate (21.71 g, 157.1 mmol) was formed in acetone (200 mL). To this suspension dimethyl sulfate (10.90 mL, 115.2 mmol) was slowly added. The reaction mixture was stirred at 60 °C for 2 h. After completion of the reaction, it was cooled to room temperature and subsequently concentrated under reduced pressure to remove the solvent. The concentrated residue was dissolved in a mixture of ether (200 mL) and water (100 mL) to separate the organic phase. The organic phase was washed sequentially with 2N aqueous hydrochloric acid (50 mL) and saturated sodium bicarbonate solution (50 mL), and then dried with anhydrous magnesium sulfate. The dried organic phase was evaporated from the solvent under reduced pressure to give the light yellow oily product 2-bromo-5-fluoroanisole (21.46 g, 100% yield). The product was confirmed by NMR hydrogen spectrum (300 MHz, CDCl3): δ 7.45 (1H, dd, Ar-H), 6.70-6.55 (2H, m, Ar-H), 3.90 (3H, s, OCH3).
References
[1] Patent: WO2004/43903, 2004, A1. Location in patent: Page 29
[2] Patent: WO2004/43903, 2004, A1. Location in patent: Page 30
[3] Patent: WO2004/43904, 2004, A1. Location in patent: Page 28
