Methyl 2-(bromomethyl)-4-methoxybenzoate Chemical Properties

Melting point:

51 °C

Boiling point:

350.4±32.0 °C(Predicted)

Density 

1.432±0.06 g/cm3(Predicted)

storage temp. 

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

Appearance

White to off-white Solid

Methyl 2-(bromomethyl)-4-methoxybenzoate Usage And Synthesis

Uses

Methyl 2-(bromomethyl)-4-methoxybenzoate

Synthesis

The general procedure for the synthesis of methyl 2-bromomethyl-4-methoxybenzoate from methyl 4-methoxy-2-methylbenzoate was as follows: N-bromosuccinimide (1.1 g, 6.2 mmol) and a catalytic amount of methyl 4-methoxy-2-methylbenzoate (1 g, 5.6 mmol) were pre-dissolved in carbon tetrachloride (5 mL), which was subsequently added dropwise to a solution containing 25 mL of carbon tetrachloride. After addition of benzoyl peroxide, the reaction mixture was refluxed for 2 hours. After completion of the reaction, it was cooled to room temperature and the mixture was poured into ice water. The aqueous phase was extracted with dichloromethane (3×), and the combined organic phases were dried over magnesium sulfate, filtered, and concentrated under vacuum to afford 2.1 g of the target product, methyl 2-bromomethyl-4-methoxybenzoate, as a light yellow solid in about 100% yield. Mass spectrometry analysis showed [M + H+] m/z 260.

References

[1] Patent: WO2011/85261, 2011, A1. Location in patent: Page/Page column 36
[2] Patent: WO2011/85128, 2011, A1. Location in patent: Page/Page column 56
[3] Journal of Medicinal Chemistry, 1987, vol. 30, # 10, p. 1798 - 1806
[4] Patent: US2008/249101, 2008, A1. Location in patent: Page/Page column 40
[5] Patent: WO2008/20306, 2008, A2. Location in patent: Page/Page column 35

Methyl 2-(bromomethyl)-4-methoxybenzoate(15365-25-0)Related Product Information

• METHOXYTRIMETHYLSILANE
• Methyl 2-iodobenzoate
• Methyl 3-(bromomethyl)benzoate
• Methyl 4-(bromomethyl)benzoate
• Methyl 4-cyanobenzoate
• METSULFURON METHYL
• Bensulfuron methyl
• Methylparaben
• 4-Methoxybenzoic acid
• Methyl benzoate
• Methyl salicylate
• Kresoxim-methyl
• 4-Bromomethylbenzoic acid
• Methyl acetate
• Thiophanate-methyl
• Methyl
• Methyl 2-bromomethylbenzoate
• 2-(Bromomethyl)benzoic acid