Dichloromethylation of Nitrobenzene Derivatives via Vicarious Nucleophilic Substitution of Hydrogen with Trichloromethyl Carbanions in Flow

In recent years, indigo compounds have been adopted across a wide range of applications. Of particular interest has been their use as organic semiconductors. As this field has expanded, increased efforts have been directed toward probing the structure of these compounds to develop semiconductors with improved charge transport properties. One strategy that has been employed involves the functionalisation of the core indigo structure. This has been achieved using functionalised nitrobenzaldehyde starting materials, which are generated via hydrolysis of dichloromethylated intermediates. However, since these intermediates are often costly or commercially unavailable, it has been considered advantageous for a cost-effective procedure to be established for the large-scale synthesis of the required aldehyde precursors.

In this work, a cost-effective synthesis of dichloromethylated nitroarene intermediates on a gram scale is reported. This has been accomplished using vicarious nucleophilic substitution in combination with flow chemistry, allowing simplified access to a range of halogenated nitrobenzaldehydes. As a result, the generation and investigation of structurally diverse indigo-based semiconductors may be facilitated.

• Lyall-Brookes, G

• Trichloromethyl Carbanions in Flow , Durham theses, Durham University

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