1-(4-BROMO-PHENYL)-2-PYRIDIN-4-YL-ETHANONE

1-(4-BROMO-PHENYL)-2-PYRIDIN-4-YL-ETHANONE Property

storage temp. 

Sealed in dry,Room Temperature

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

1-(4-BROMO-PHENYL)-2-PYRIDIN-4-YL-ETHANONE Chemical Properties,Usage,Production

Synthesis

A THF (50 mL) solution of LDA (51 mL, 2 M solution of THF) was cooled to 0 °C under nitrogen protection. 4-Methylpyridine (9.5 g, 102 mmol) was added slowly and the reaction was kept for 30 min. Subsequently, the reaction system was cooled to -65 °C. In another round-bottom flask, 4-bromo-N-methoxy-N-methylbenzamide was dissolved in THF (50 mL) and cooled to -65 °C under nitrogen protection. A freshly prepared 4-methylpyridine anionic solution (1.2 eq.) was slowly added to the above cooled amide solution over 45 min. After continued stirring for 30 minutes, acetic acid (50 mL) was slowly added and the reaction mixture was gradually warmed to room temperature. The pH of the mixture was adjusted to 7 with base and subsequently extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was recrystallized by a solvent mixture of petroleum ether and ethyl acetate (10:1, v/v) to give 1-(4-bromophenyl)-2-(4-pyridinyl)-ethanone (5.2 g, 92% yield) as a yellow solid. Mass spectrum (ESI) m/z = 276 [M + H]+.

References

[1] Patent: US2013/158031, 2013, A1. Location in patent: Paragraph 0180; 0181
[2] MedChemComm, 2013, vol. 4, # 2, p. 443 - 449