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The transposition of Sandmeyer chlorination from a batch to a safe continuous-flow process was investigated. Our initial approach was to develop a cascade method using flow chemistry which involved the generation of a diazonium salt and its quenching with copper chloride. To achieve this safe continuous process diazotation, a chemometric approach (Simplex method) was used and extrapolated to establish a fully continuous-flow method. The reaction scope was also examined via the synthesis of several (het)aryl chlorides. Validation and scale-up of the process were also performed. A higher productivity was obtained with increased safety.
Efficient Transposition of the Sandmeyer Reaction from Batch to Continuous Process
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, and Sylvain Routier*† Image may be NSFW.Clik here to view.
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1H NMR (250 MHz, Chloroform-d) δ 7.65 (dd, J = 2.1, 0.6 Hz, 1H, Har), 7.42 (dd, J = 8.7, 0.6 Hz, 1H, Har), 7.32 (dd, J = 8.7, 2.0 Hz, 1H, Har).
2,5-Dichloro-1,3-benzoxazole (33)
1H NMR PREDICT
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13 C NMR PREDICT
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