Uses
It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs.
Synthesis
The general procedure for the synthesis of 2-bromobenzaldehyde vinyl aldehyde from ethylene glycol and o-bromobenzaldehyde was as follows: to a solution of benzene (40 mL) containing 2-bromobenzaldehyde (5.30 mmol) was added ethylene glycol (1.26 mL, 22.6 mmol, 4.3 eq.) and p-toluenesulfonic acid (70 mg, 0.37 mmol, 0.07 eq.) in sequence. The reaction mixture was placed in a Dean-Stark apparatus and heated to reflux. After 4 hours of reaction, the reaction was cooled to room temperature and quenched with triethylamine, followed by concentration of the reaction solution under reduced pressure. Finally, purification by silica gel column chromatography afforded the target product 2-bromobenzaldehyde vinyl aldehyde in quantitative yield.
References
[1] Patent: US2004/147401, 2004, A1. Location in patent: Page 33
[2] Organic and Biomolecular Chemistry, 2009, vol. 7, # 6, p. 1106 - 1114
[3] Organic Letters, 2013, vol. 15, # 18, p. 4718 - 4721
[4] European Journal of Organic Chemistry, 2014, vol. 2014, # 10, p. 2084 - 2091
[5] Organic Process Research and Development, 2016, vol. 20, # 2, p. 253 - 261
