Benzoic acid,5-broMo-2-(trifluoroMethyl)-,Methyl ester

Benzoic acid,5-broMo-2-(trifluoroMethyl)-,Methyl ester Property

Boiling point:

280.9±40.0 °C(Predicted)

Density 

1.598±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

liquid

color 

Clear, faint to light yellow

Safety

HS Code 

2916310090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

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

Benzoic acid,5-broMo-2-(trifluoroMethyl)-,Methyl ester Chemical Properties,Usage,Production

Synthesis

A. Synthesis of methyl 5-bromo-2-(trifluoromethyl)benzoate. Methyl 5-bromo-2-iodobenzoate (4.65 g, 13.64 mmol) and methyl fluorosulfonyl difluoroacetate (2.6 mL, 20.44 mmol) were dissolved in N-methyl-2-pyrrolidone (10 mL) under nitrogen protection. Copper (I) bromide (235 mg, 1.638 mmol) was subsequently added. The reaction mixture was transferred to a sealed tube and the reaction was stirred at 120 °C for 15 hours. After completion of the reaction, the mixture was cooled to room temperature, diluted with ethyl acetate and washed with saturated aqueous sodium chloride solution. The aqueous phase was back-extracted with ethyl acetate (3 x 25 mL), the organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by concentration under reduced pressure. The residue was purified by silica gel column chromatography with hexane solution of 1-5% ethyl acetate as eluent to afford methyl 5-bromo-2-trifluoromethylbenzoate as a colorless oil (2.9 g, 10.25 mmol, 75% yield). The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 8.08 (s, 1H), 8.01 (d, J = 8.20 Hz, 1H), 7.83 (d, J = 8.20 Hz, 1H), 3.90 (s, 3H).

References

[1] Patent: WO2009/89042, 2009, A1. Location in patent: Page/Page column 101