2-Bromo-4-chlorobenzaldehyde

Chemical Properties

Yellow crystalline

Uses

2-Bromo-4-chlorobenzaldehyde is an important organic synthesis intermediate and pharmaceutical intermediate, widely used in laboratory research and chemical production processes.

Synthesis

General procedure for the synthesis of 4-chloro-2-bromobenzaldehyde from (2-bromo-4-chlorophenyl)methanol: Pyridinium chlorochromate (432 mg, 2 mmol) was added to a solution of 2-bromo-4-chlorobenzyl alcohol (200 mg, 0.9 mmol) in dichloromethane (4 mL). The reaction mixture was stirred at room temperature for 2 hours. After the reaction was complete, ether (4 mL) was added and stirring was continued for 20 minutes. The mixture was poured into ether and the remaining solid was washed twice with ether. All ether solutions were combined and concentrated under reduced pressure. The product was purified by silica gel column chromatography with an eluent ratio of 20:80 to 1:1 ethyl acetate:dichloromethane to give 4-chloro-2-bromobenzaldehyde as a white solid (167 mg, 85% yield).

References

[1] Patent: WO2006/44454, 2006, A1. Location in patent: Page/Page column 47
[2] Patent: WO2010/55005, 2010, A1. Location in patent: Page/Page column 72-73
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 23, p. 6463 - 6466