Synthesis
GENERAL METHOD: A mixture of 2-chloro-6-fluorobenzyl alcohol (1.0 mmol), N-phenylglycine (0.0076 g, 0.05 mmol), CuBr2 (0.0112 g, 0.05 mmol), Na2CO3 (0.1060 g, 1.0 mmol), and TEMPO (0.0078 g, 0.05 mmol) was added to a 100 mL Schlenk tube with H2O (3.0 mL) was added to a 100 mL Schlenk tube. It was stirred vigorously for 0.5 h under reflux conditions in air. After completion of the reaction, the product was extracted with CH2Cl2 (3 x 2.0 mL). The organic phases were combined, washed with H2O (3.0 mL) and dried with anhydrous MgSO4. After vacuum concentration, the residue was purified by column chromatography to give 2-chloro-6-fluorobenzaldehyde. Isolated yield: 0.1080 g (90%).
References
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[2] Journal of the American Chemical Society, 2011, vol. 133, # 42, p. 16901 - 16910
[3] RSC Advances, 2014, vol. 4, # 90, p. 48777 - 48782
[4] Journal of Organic Chemistry, 2015, vol. 80, # 21, p. 11184 - 11188
[5] Synlett, 2015, vol. 26, # 6, p. 779 - 784