Methyl 3-bromomethyl-4-cyanobenzoate Chemical Properties

Boiling point:

355.7±37.0 °C(Predicted)

Density 

1.53±0.1 g/cm3(Predicted)

storage temp. 

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

Appearance

White to off-white Solid

Methyl 3-bromomethyl-4-cyanobenzoate Usage And Synthesis

Synthesis

The general procedure for the synthesis of methyl 2-(bromomethyl)-3-cyanobenzoate from methyl 3-cyano-2-methylbenzoate was as follows: under nitrogen protection, methyl 3-cyano-2-methylbenzoate (10.6 g, 60.5 mmol), N-bromosuccinimide (NBS) (16.2 g, 90.7 mmol), and azobisisobutyronitrile (AIBN) ( 100 mg) were suspended in tetrachloromethane (200 mL) and reacted at reflux for 6 hours. As an alternative, benzoyl peroxide can be used as a catalyst for the bromination reaction in benzene. The progress of the reaction was monitored by thin layer chromatography (TLC) (unfolding agent: hexane solution of 10% ethyl acetate) to confirm complete consumption of the feedstock. After completion of the reaction, the reaction mixture was filtered and the filter cake was washed with chloroform (3 x 20 mL). The filtrate and washings were combined and concentrated under reduced pressure. The residue was purified by short silica gel column chromatography using a hexane solution of 10% ethyl acetate as eluent. The eluate containing the target product was collected and concentrated under reduced pressure, and the resulting product was dried overnight under vacuum to afford methyl 2-(bromomethyl)-3-cyanobenzoate 15.1 g in 98% yield. 1H NMR data of the product (DMSO-d6): δ 8.15 (d, J = 8.0 Hz, 1H); 8.12 (d, J = 7.9 Hz, 1H); 7.67 (t, 1H); 5.04 (s, 2H); 3.89 (s, 3H).

References

[1] Patent: US2007/49555, 2007, A1. Location in patent: Page/Page column 94
[2] Patent: WO2008/106619, 2008, A2. Location in patent: Page/Page column 581

Methyl 3-bromomethyl-4-cyanobenzoate(908562-24-3)Related Product Information

• Methyl 2-bromomethyl-4-cyanobenzoate
• Methyl 2-(Bromomethyl)-3-Cyanobenzoate
• Methyl 3-(bromomethyl)benzoate
• Methyl 3-bromomethyl-4-cyanobenzoate
• 3-(BROMOMETHYL)BENZOIC ACID
• Methyl 4-cyanobenzoate
• (3-(BROMOMETHYL)PHENYL)METHANOL
• 4-Cyanobenzoic acid
• 2-Cyanobenzyl bromide