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Entry 1). Although higher concentrations resulted in higher
yields (Entries 2–4), the 45 wt % aq. NaOH solution was
found to cause an injection problem because of high viscosity
and microchannel clogging (Entry 4). We also investigated
the yield in terms of the organic to aqueous phase injection
ratio and observed that an increase in the injection ratio of
aq. NaOH resulted in higher yields (Entries 3, 5, and 6).
We performed dichlorocyclopropanation of various sty-
rene derivatives under the optimized conditions (Table 4).
Starting with α-methylstyrene, a low yield of 67% was
obtained with the batch process after 1 h, while a high yield
of 93% was obtained after just 20 min with the continuous
flow process (Entry 1). Dichlorocyclopropanation of
p-chlorostyrene and p-methoxystyrene, which are styrene
derivatives with functional groups at the para position,
resulted in yields of 88 and 99%, respectively, with the flow
process (Entries
2
and 3). Starting with styrene,
(2,2-dichlorocyclopropyl)benzene was obtained in 90% yield
with the batch process, but the yield increased to 95% with
the flow process (Entry 4). The yields were also examined for
different inner diameters (IDs) of the microchannel. As the ID
was increased, the reaction yields decreased slightly (Entry 4),
but the throughput increased from 2.41 g/h (ID: 1.5 mm) to
3.46 g/h (ID: 1.9 mm) and 5.13 g/h (ID: 2.4 mm) (See
section 5 in the supporting information for more details).
Acknowledgments. We gratefully acknowledge financial
support from the National Research Foundation of Korea
(NRF-2014R1A6A9064166, and NRF-2020R1F1A1073052).
ꢀ
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Supporting Information. Additional supporting informa-
tion may be found online in the Supporting Information
section at the end of the article.
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Bull. Korean Chem. Soc. 2021
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