4-Chloro-3-fluorophenol

Chemical Properties

White to salmon crystalline solid

Uses

4-Chloro-3-fluorophenol was used in the synthesis of 4-chloro-3-fluoro catechol and 5-Chloro-4-fluoro-2-hydroxyacetophenone.

General Description

4-Chloro-3-fluorophenol is hydroxylated at both ortho positions to yield different products.

Synthesis

GENERAL METHOD: [2-(Phenoxy)-ethyl]-trimethyl-silane (195 mg, 1.0 mmol) was dissolved in anhydrous DMF (2 mL), cesium fluoride (576 mg, 3.0 mmol) was added, and the reaction was stirred for 1 hr at 60 °C. After the reaction was completed, the reaction mixture was diluted with water and extracted with ethyl acetate (3 × 20 mL). The organic layers were combined, washed sequentially with water and saturated saline, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford 92 mg of 4-chloro-3-fluorophenol in 93% yield. The 1H NMR data of the compound was consistent with the standard, confirming its structure.

References

[1] ISHIKAWA Y. 6-Chloro-7-fluoro-4-oxo-4H-chromene-3-carbaldehyde.[J]. Acta crystallographica. Section E, Structure reports online, 2014, 70 Pt 7: o825. DOI:10.1107/S1600536814014706.
[2] VIDYA S. SHIVATARE W. T. Vibronic and cation spectroscopy of selected rotamers of 4-chloro-3-fluorophenol[J]. Molecular Physics, 2014, 112 1: 2397-2406. DOI:10.1080/00268976.2014.904050.