2-BROMOMETHYL-4-CHLORO-BENZOIC ACID METHYL ESTER

2-BROMOMETHYL-4-CHLORO-BENZOIC ACID METHYL ESTER Property

storage temp. 

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

Safety

RIDADR 

3261

HazardClass 

8

PackingGroup 

Ⅱ

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H317May cause an allergic skin reaction

H319Causes serious eye irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2-BROMOMETHYL-4-CHLORO-BENZOIC ACID METHYL ESTER Chemical Properties,Usage,Production

Synthesis

Methyl 4-chloro-2-methylbenzoate (10.86 g, 58.8 mmol, 1.0 eq.) was used as the starting material and dissolved in carbon tetrachloride (100 mL). N-bromosuccinimide (15.7 g, 88.2 mmol, 1.5 eq.) and benzoyl peroxide (0.05 g) were added sequentially. The reaction mixture was heated to reflux overnight. After completion of the reaction, the reaction mixture was filtered and the solids were washed with dichloromethane. The organic filtrates were combined, concentrated and dried to afford the target product methyl 2-bromomethyl-4-chlorobenzoate (7.1 g, 45.8% yield). The structure of the product was confirmed by 1H NMR.

References

[1] Patent: US2005/143348, 2005, A1. Location in patent: Page/Page column 45; 49; 55
[2] Patent: US2005/239838, 2005, A1. Location in patent: Page/Page column 41
[3] Patent: WO2005/54176, 2005, A1. Location in patent: Page/Page column 136
[4] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 5, p. 1628 - 1631
[5] Patent: US2009/270393, 2009, A1. Location in patent: Page/Page column 43-44