Methyl 4-Bromo-3-(Trifluoromethyl)benzoate Chemical Properties

Boiling point:

274℃

Density 

1.598

Flash point:

120℃

storage temp. 

2-8°C

form 

Solid

Appearance

White to off-white Solid

InChI

InChI=1S/C9H6BrF3O2/c1-15-8(14)5-2-3-7(10)6(4-5)9(11,12)13/h2-4H,1H3

InChIKey

DTVRLJMSCKUEEN-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC=C(Br)C(C(F)(F)F)=C1

Safety Information

HS Code 

2916310090

Methyl 4-Bromo-3-(Trifluoromethyl)benzoate Usage And Synthesis

Synthesis

Thionyl chloride (16.2 mL, 223 mmol) was slowly added dropwise to a suspension of 4-bromo-3-(trifluoromethyl)benzoic acid (15.0 g, 55.8 mmol) in methanol (300 mL) over 15 minutes. The reaction mixture was stirred at room temperature for 12 hours. Subsequently, the reaction mixture was concentrated by distillation under reduced pressure. The concentrated residue was dissolved in ethyl acetate (500 mL) and washed sequentially with saturated aqueous sodium bicarbonate (200 mL), water (200 mL) and brine (200 mL). The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure to give methyl 3-trifluoromethyl-4-bromobenzoate as an orange solid (14.8 g, 94% yield). High performance liquid chromatography (Method A) showed a retention time of 4.7 min (purity: 99.0%).1H NMR (DMSO-d6, 300 MHz) δ 8.26 (m, 1H), 8.14 (m, 2H), 3.93 (s, 3H).

References

[1] Patent: WO2010/100142, 2010, A1. Location in patent: Page/Page column 54

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