Paper
Green Chemistry
Procedure for the synthesis of α-haloketones 5a and 5b
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To a sealed tube were added alkyne (0.25 mmol, 25.5 mg),
DBDMH (0.3 mmol, 86 mg), ethylene thiourea (0.0375 mmol),
and water (1 mL), then the contents were stirred at 45 °C. After
completion of the reaction (monitored by TLC), the solution
was concentrated under reduced pressure to remove water.
2-Amino(thio)phenols (0.2 mmol), Et2NH (0.8 mmol, 60 mg),
and DMF (0.5 mL) were stirred at 90 °C under N2 for another
5 h. After cooling to room temperature, water (20 mL) was
added, and the aqueous phase was extracted with ethyl acetate
(5 × 20 mL). The combined organic phases were dried over
Na2SO4, and concentrated under vacuum. The residue was pur-
ified by column chromatography on silica gel (eluent: hexanes/
ethyl acetate) to afford benzo[d]oxazol-2-yl(phenyl)methanone
5a and benzo[d]thiazol-2-yl(phenyl)methanone 5b.
Acknowledgements
We are grateful for financial support from the National Natural
Science Foundation of China (No. 21302048), the Hunan
Provincial Natural Science Foundation of China (No. 14JJ7028),
the Science and Technology Innovative Research Team in
Higher Educational Institutions of Hunan Province (2012-318),
Scientific Research Hunan Provincial Education Department
(No. 15B095 and 13CY029). Authors wish to thank Bruker
Daltonics for assistance with HRMS (ESI) Analysis.
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