Synthesis
General procedure for the synthesis of 5-bromoisophthalaldehyde from 5-bromo-1,3-dihydroxymethylbenzene: Manganese(IV) dioxide (35.5 g, 408 mmol) was added to a solution of 5-bromo-1,3-phenylenedimethanol (3.60 g, 16.6 mmol) in tetrahydrofuran (250 mL) and the reaction was heated for 4 hr at 60 °C. Upon completion of the reaction, the reaction mixture was filtered through diatomaceous earth and the filtrate was concentrated under reduced pressure to remove the solvent. The final 5-bromoisophthalaldehyde (1.61 g, 46% yield) was obtained as a white solid.
References
[1] Tetrahedron Letters, 2000, vol. 41, # 7, p. 1015 - 1018
[2] Synthesis, 1998, # 12, p. 1742 - 1749
[3] Chemische Berichte, 1989, vol. 122, p. 1365 - 1372
[4] New Journal of Chemistry, 2009, vol. 33, # 2, p. 345 - 357
[5] Patent: JP2015/224231, 2015, A. Location in patent: Paragraph 0071
