4-Bromo-2-fluoro-3-methylbenzonitrile

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4-Bromo-2-fluoro-3-methylbenzonitrile Basic information
Product Name:4-Bromo-2-fluoro-3-methylbenzonitrile
Synonyms:4-Bromo-2-fluoro-3-methylbenzonitrile;Benzonitrile, 4-bromo-2-fluoro-3-methyl-;4-bromo-2-fluoro-3-methylbenzene-1-carbonitrile
CAS:1114546-30-3
MF:C8H5BrFN
MW:214.03
EINECS:
Product Categories:
Mol File:1114546-30-3.mol
4-Bromo-2-fluoro-3-methylbenzonitrile Structure
4-Bromo-2-fluoro-3-methylbenzonitrile Chemical Properties
Boiling point 259.6±35.0 °C(Predicted)
density 1.59±0.1 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
form crystalline powder
color Wooly, light pinkish peach
Safety Information
HS Code 2926907090
MSDS Information
4-Bromo-2-fluoro-3-methylbenzonitrile Usage And Synthesis
Synthesis
Benzonitrile, 4-amino-2-fluoro-3-methyl- (9CI)

757247-93-1

4-Bromo-2-fluoro-3-methylbenzonitrile

1114546-30-3

Using 4-amino-2-fluoro-3-methylbenzonitrile (10 g, 66.6 mmol) as starting material, potassium nitrite (22.67 g, 266 mmol) and copper (I) bromide (1.911 g, 13.32 mmol) were dissolved in dimethyl sulfoxide (400 mL). Subsequently, 48% aqueous hydrogen bromide solution (33 mL, 266 mmol) diluted with dimethyl sulfoxide (200 mL) was added dropwise and the reaction mixture was stirred for 2 hours. Upon completion of the reaction, complete conversion of the feedstock was confirmed by thin layer chromatography (TLC) monitoring. The reaction mixture was slowly poured into ice-cold water and neutralized with cold concentrated sodium hydroxide solution to pH 7. The precipitated solid was collected by filtration to afford the target product 4-bromo-2-fluoro-3-methylbenzonitrile (11.4 g, 53.3 mmol, 80% yield) as a white solid. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 7.47 (d, J = 9.37 Hz, 1H), 7.33 (t, 1H), 2.39 (d, J = 2.34 Hz, 3H).

References[1] Patent: WO2010/62571, 2010, A1. Location in patent: Page/Page column 128
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