Methyl 2-bromo-3-methylbenzoate Chemical Properties

Boiling point:

267.4±20.0 °C(Predicted)

Density 

1.433±0.06 g/cm3(Predicted)

refractive index 

1.5530 to 1.5570

storage temp. 

Inert atmosphere,Room Temperature

form 

Liquid

color 

Red

Water Solubility 

Slightly soluble in water.

CAS DataBase Reference

131001-86-0

Safety Information

HS Code 

2916310090

Methyl 2-bromo-3-methylbenzoate Usage And Synthesis

Chemical Properties

brown liquid

Uses

Methyl 2-bromo-3-methylbenzoate is used as pharmaceutical intermediate.

Synthesis

A mixed solution of 2-bromo-3-methylbenzoic acid (5 g, 23.2 mmol) and concentrated sulfuric acid (0.5 mL) in anhydrous methanol (100 mL) was heated to reflux for 20 hours. Upon completion of the reaction, the solvent was removed by concentration under reduced pressure by rotary evaporator. The concentrated residue was dissolved in dichloromethane (50 mL) and washed with saturated sodium bicarbonate solution (30 mL) to neutralize the acid. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated again under reduced pressure by rotary evaporator to afford methyl 2-bromo-3-methylbenzoate (4.43 g, 19.3 mmol, 83% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 2.46 (s, 3H), 3.93 (s, 3H), 7.24 (t, J = 8.0 Hz, 1H), 7.34 (dd, J = 1.0 Hz, J = 8.0 Hz, 1H), 7.46 (dd, J = 1.0 Hz, J = 8.0 Hz, 1H).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 2, p. 644 - 651
[2] Journal of the American Chemical Society, 2016, vol. 138, # 18, p. 5813 - 5816
[3] Patent: WO2004/37806, 2004, A1. Location in patent: Page 45
[4] Patent: WO2018/205948, 2018, A1. Location in patent: Page/Page column 49
[5] Patent: WO2004/37806, 2004, A1. Location in patent: Page 71

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