Ethyl 2-(4-broMopyridin-2-yl)acetate Chemical Properties

Boiling point:

294.4±25.0 °C(Predicted)

Density 

1.451±0.06 g/cm3(Predicted)

storage temp. 

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

pka

2.87±0.10(Predicted)

Appearance

Light yellow to yellow Liquid

InChI

InChI=1S/C9H10BrNO2/c1-2-13-9(12)6-8-5-7(10)3-4-11-8/h3-5H,2,6H2,1H3

InChIKey

UNQUMGSSWNEUIM-UHFFFAOYSA-N

SMILES

C1(CC(OCC)=O)=NC=CC(Br)=C1

Ethyl 2-(4-broMopyridin-2-yl)acetate Usage And Synthesis

Synthesis

General procedure for the synthesis of ethyl 2-(4-bromopyridin-2-yl)acetate from 4-bromo-2-methylpyridine and diethyl carbonate: Step 1: Synthesis of ethyl 2-(4-bromopyridin-2-yl)acetate Under nitrogen protection, 4-bromo-2-methylpyridine (2.00 g) and diethyl carbonate (1.8 mL) were dissolved in anhydrous tetrahydrofuran (30 mL) and cooled to -70°C. Lithium diisopropylammonium (2 mol/L in tetrahydrofuran/heptane/ethylbenzene, 3.00 mL) was slowly added and the reaction was stirred by keeping the temperature at -70°C for 1 hour. Subsequently, lithium diisopropylammonium (2 mol/L in tetrahydrofuran/heptane/ethylbenzene, 3.00 mL) was added again and stirring was continued at -70°C for 1 hour. Upon completion of the reaction, the reaction was quenched by the addition of water. The reaction mixture was extracted with ethyl acetate, the organic phases were combined, washed with saturated brine and dried over anhydrous sodium sulfate. The organic phase was concentrated under reduced pressure and the resulting crude product was purified by silica gel column chromatography (eluent: cyclohexane/ethyl acetate, 95:5→1:1) to give ethyl 2-(4-bromopyridin-2-yl)acetate. Yield: 2.35 g (83% yield). LC (Method 3): tR = 2.86 min; MS (ESI+): m/z = 244/246 (Br)[M + H]+.

References

[1] Patent: WO2011/159760, 2011, A1. Location in patent: Page/Page column 73
[2] Patent: WO2018/106636, 2018, A1. Location in patent: Paragraph 00244
[3] Patent: WO2017/74833, 2017, A1. Location in patent: Page/Page column 61; 80; 81