A selective photochemical monochlorination of 2-fluorotoluene has been developed by a continuous flow process using two different flow reactors, one for the tuning of the conditions and the second one for the scale-up. The key reaction parameters were optimized using one-factor-at-a-time and design of experiment methods, with the goal of minimizing the formation of the dichlorinated by-product. This transformation has been performed on a multi decagram scale.
This
study describes our recent efforts to find an efficient and
scalable route to tetrahydro-4H-pyran-4-one using
the commercially available starting materials. The route scouting
work and the full development of an efficient access to the target
are described. This work culminated in the preparation of above 20
kg of the title compound in our pilot plant facility.
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