METHYL 2-BROMOMETHYL-3-CHLORO-BENZOATE Chemical Properties

Boiling point:

331.0±32.0 °C(Predicted)

Density 

1.561±0.06 g/cm3(Predicted)

storage temp. 

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

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C9H8BrClO2/c1-13-9(12)6-3-2-4-8(11)7(6)5-10/h2-4H,5H2,1H3

InChIKey

BZXFVKQUKUJTIM-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC=CC(Cl)=C1CBr

Safety Information

RIDADR 

3261

HazardClass 

8

PackingGroup 

Ⅱ

METHYL 2-BROMOMETHYL-3-CHLORO-BENZOATE Usage And Synthesis

Synthesis

Methyl 3-chloro-2-methylbenzoate (1 g, 5.42 mmol) was used as a raw material, which was mixed with carbon tetrachloride (13.3 ml), N-bromosuccinimide (1.06 g, 5.96 mmol) and benzoyl peroxide (3.5 mg, 0.0108 mmol) to form a suspension. The reaction mixture was heated in an oil bath at 90°C under nitrogen protection. After the reaction was carried out for 3 hours and 45 minutes, the heating was stopped. The reaction solution was sequentially diluted with water, ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was separated, washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, filtered and concentrated to afford the target product methyl 2-bromomethyl-3-chloro-benzoate (1.43 g, yield: 100%). The product was characterized by 1H-NMR (400 MHz, CDCl3) with chemical shifts δppm of 4.00 (3H, s), 5.12 (2H, s), 7.32 (1H, t, J = 8 Hz), 7.58 (1H, dd, J = 2,8 Hz), 7.86 (1H, dd, J = 2,8 Hz), respectively.

References

[1] Patent: US2013/65925, 2013, A1. Location in patent: Paragraph 0338; 0339
[2] Patent: EP2757103, 2014, A1. Location in patent: Paragraph 0215
[3] Patent: US5958968, 1999, A
[4] Patent: WO2004/58717, 2004, A1. Location in patent: Page 77
[5] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 360 - 365

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