6-Bromo-2-hydroxy-3-methoxybenzaldehyde

Uses

6-Bromo-2-hydroxy-3-methoxybenzaldehyde may be used in the synthesis of:

• 2-benzyloxy-6-bromo-3-methoxybenzaldehyde
• biphenyls
• antihypertensive natural products S-(+)-XJP and R-(-)-XJP

General Description

6-Bromo-2-hydroxy-3-methoxybenzaldehyde is a bromobenzaldehyde derivative. It participates in the synthesis of (±)-norannuradhapurine. Its crystals exhibit monoclinic crystal system and space group P2₁/n.

Synthesis

2-Acetoxy-3-methoxy-6-bromobenzaldehyde (48.2 g, 176.5 mmol) was used as starting material and dissolved in methanol (500 mL). Subsequently, 6 N hydrochloric acid (500 mL) was slowly added and the reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the product was separated by diafiltration. The filter cake was washed with petroleum ether (100 mL × 3) and subsequently dried under vacuum to afford the yellow solid product 6-bromo-2-hydroxy-3-methoxybenzaldehyde (40.4 g, 99% yield).

References

[1] Patent: CN108358761, 2018, A. Location in patent: Paragraph 0042; 0043; 0078; 0079; 0096; 0097; 0105; 0106
[2] Journal of Medicinal Chemistry, 2000, vol. 43, # 14, p. 2731 - 2737
[3] Patent: US2003/220304, 2003, A1
[4] Patent: US2006/293394, 2006, A1. Location in patent: Figure 12
[5] Tetrahedron Letters, 2003, vol. 44, # 27, p. 5129 - 5132