Trifluoromethylated hydroquinone derivatives and method for producing the same

One-step method for producing trifluoromethylated hydroquinones via visible light irradiation

This technology is a manufacturing method that obtains trifluoromethylated hydroquinone derivatives in a single step by irradiating benzoquinone derivatives with 380–500 nm visible light in a solvent containing a trifluoromethylating reagent. It utilizes a reaction pathway where a quinhydrone intermediate, generated by light irradiation, reacts with the reagent.

Previously, introducing a trifluoromethyl group into hydroquinone required synthesizing the hydroquinone first, followed by a separate substitution reaction. This process necessitated harsh reaction conditions and typically resulted in low yields of only 30–50%.

This technology uses affordable, readily available benzoquinone derivatives and Langlois reagent as starting materials to obtain the target compound at room temperature with high yields, without the need for separate substitution steps. The process is simplified as the reaction proceeds using a low-power blue LED light source instead of UV lamps or high-output xenon lamps. It can be applied to the synthesis of antioxidants, polymerization inhibitors, whitening agents, and pharmaceutical and agricultural intermediates, enabling the economical mass production of fluorine-substituted hydroquinones.

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Key Features:

• A step of reacting a benzoquinone derivative in a solvent in the presence of a trifluoromethylating reagent by irradiating it with light at a wavelength of 380 nm to 500 nm
• A reaction mechanism in which the benzoquinone derivative forms a quinhydrone derivative upon light irradiation, which then reacts with the trifluoromethylating reagent
• A configuration using 1,4-benzoquinone, which may be unsubstituted or substituted with C1-C10 alkyl, alkoxy, or halogen groups, and Langlois reagent
• Reaction conditions performed at room temperature in a solvent mixture of water and acetonitrile or 2,2,2-trifluoroethanol in a volume ratio of 1:2 to 2:1

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This invention was developed with support from the Ministry of Science and ICT for research on the development and application of organic photoreactions.

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