5-BROMO-2,4-DIMETHYLPYRIDINE Chemical Properties

Boiling point:

205-210 °C

Density 

1.415±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

4.25±0.18(Predicted)

Appearance

Light yellow to gray Liquid

InChI

InChI=1S/C7H8BrN/c1-5-3-6(2)9-4-7(5)8/h3-4H,1-2H3

InChIKey

SLMUXUHXAIPROA-UHFFFAOYSA-N

SMILES

C1(C)=NC=C(Br)C(C)=C1

Safety Information

HS Code 

2933399990

5-BROMO-2,4-DIMETHYLPYRIDINE Usage And Synthesis

Synthesis

A solution of 2,5-dibromo-4-methylpyridine (2.51 g, 10.0 mmol) in anhydrous THF (50 mL) was added to a three-necked flask, followed by tetrakis(triphenylphosphine)palladium (1.15 g, 1.0 mmol). The reaction mixture was cooled to 0 °C under nitrogen protection and stirred. A THF solution of methylmagnesium bromide (15 mL, 15.0 mmol, 1 mol/L) was added slowly and dropwise. After the dropwise addition, the reaction mixture was heated to reflux for 3 hours. After completion of the reaction, it was cooled to room temperature, the reaction was quenched with 1N hydrochloric acid and extracted with ethyl acetate (100 mL x 3). The organic layers were combined, washed sequentially with water (50 mL x 2) and saturated saline (50 mL) and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the crude product was purified by Biotage fast chromatography (petroleum ether/ethyl acetate = 5%-10%) to afford 2,4-dimethyl-5-bromopyridine (301 mg, 16.2%) as a colorless oil.1H NMR (400 MHz, CDCl3) δppm: 2.35 (d, 3H), 2.47 (s, 3H), 7.04 ( s, 1H), 8.50 (s, 1H).

References

[1] Patent: WO2017/221092, 2017, A1. Location in patent: Paragraph 00190

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