1-Bromo-2-naphthaldehyde

Chemical Properties

Light yellow solid

Uses

1-Bromo-2-naphthaldehyde is used as a reagent in the synthesis of Hoveyda-Grubbs type metathesis catalysts which are used in cross olefin metathesis. 1-Bromo-2-naphthaldehyde is also used in the preparation of novel (-)-cercosporamide derivatives as potent selective PPARγ modulators.

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 4617, 1981 DOI: 10.1021/jo00335a076

Synthesis

General procedure for the synthesis of 1-bromo-2-naphthalene formaldehyde from 1-bromo-2-(bromomethyl)naphthalene: In a 2L reactor, 4-methylmorpholine N-oxide (61.4 g, 524 mmol), molecular sieves (200 g) and acetonitrile (1.2 L) were added and stirred for 30 min at 0 °C under nitrogen protection. Subsequently, 1-bromo-2-(bromomethyl)naphthalene (78 g, 262 mmol) was added and stirring was continued for 6 hours at room temperature. After completion of the reaction, the reaction mixture was filtered and the filtrate was washed with dichloromethane. The filtrate was concentrated and purified by column chromatography to afford 1-bromo-2-naphthaldehyde (45 g) in 73% yield.

References

[1] European Journal of Organic Chemistry, 2012, # 31, p. 6155 - 6164,10
[2] European Journal of Organic Chemistry, 2012, # 31, p. 6155 - 6164
[3] Tetrahedron Letters, 1994, vol. 35, # 48, p. 8985 - 8988
[4] Patent: US2018/72753, 2018, A1. Location in patent: Paragraph 0163-0164
[5] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 9, p. 1363 - 1378