Methyl 2-(broMoMethyl)-5-cyanobenzoate Chemical Properties

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

Appearance

White to off-white Solid

Safety Information

HS Code 

2926907090

Methyl 2-(broMoMethyl)-5-cyanobenzoate Usage And Synthesis

Synthesis

B) Synthesis of methyl 2-(bromomethyl)-5-cyanobenzoate Methyl 5-cyano-2-methylbenzoate (8.9 g), N-bromosuccinimide (9.5 g), 2,2'-azobis(isobutyronitrile) (0.83 g) were mixed with (trifluoromethyl)benzene (200 mL) and the reaction was stirred for 6 hours at 80 °C under nitrogen protection. Upon completion of the reaction, the mixture was poured into water, the organic layer was separated and dried over anhydrous sodium sulfate, and subsequently concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to afford the target product methyl 2-(bromomethyl)-5-cyanobenzoate (8.05 g). The product was characterized by 1H NMR (300 MHz, CDCl3) with chemical shifts of δ3.98 (3H, s), 4.96 (2H, s), 7.61 (1H, d, J = 7.9 Hz), 7.77 (1H, dd, J = 7.9,1.9 Hz), 8.27 (1H, d, J = 1.9 Hz).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 10, p. 2823 - 2827
[2] Patent: WO2004/18414, 2004, A2. Location in patent: Page 108-109
[3] Journal of Medicinal Chemistry, 2004, vol. 47, # 3, p. 612 - 626
[4] Patent: US2017/15655, 2017, A1. Location in patent: Paragraph 1108-1109
[5] Patent: EP3327019, 2018, A1. Location in patent: Paragraph 0274