(4-BROMO-3-METHYLISOXAZOL-5-YL)METHYL ACETATE Chemical Properties

Boiling point:

289.6±35.0 °C(Predicted)

Density 

1.552±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

-2.86±0.38(Predicted)

InChI

InChI=1S/C7H8BrNO3/c1-4-7(8)6(12-9-4)3-11-5(2)10/h3H2,1-2H3

InChIKey

USGKSLUGKUUZSM-UHFFFAOYSA-N

SMILES

C(OCC1ON=C(C)C=1Br)(=O)C

Safety Information

HS Code 

2934999090

(4-BROMO-3-METHYLISOXAZOL-5-YL)METHYL ACETATE Usage And Synthesis

Synthesis

General procedure for the synthesis of (4-bromo-3-methylisoxazol-5-yl)methyl acetate from 3-methyl-5-isoxazolemethanol acetate: To a solution of (3-methylisoxazol-5-yl)methyl acetate (0.979 g, 6.31 mmol) in acetic acid (10 mL, 175 mmol) was added sequentially N-bromosuccinimide (1.30 g, 7.30 mmol) and sulfuric acid (0.65 mL, 12.19 mmol). The reaction mixture was heated to 110 °C and maintained for 1 hour. Upon completion of the reaction, the mixture was cooled to room temperature and slowly poured into a beaker containing ice and saturated sodium bicarbonate solution. The two-phase mixture was vigorously stirred and the basic aqueous phase (pH 8-9) was subsequently extracted with ethyl acetate (2 x 15 mL). The organic phase was washed sequentially with 2% sodium thiosulfate solution and brine (20 mL), dried over anhydrous sodium sulfate and concentrated to give a light yellow oil. The crude product was purified by a Biotage purification system (isocratic elution, 10% ethyl acetate: 90% hexane) to afford the title compound (4-bromo-3-methylisoxazol-5-yl)methyl acetate (1.30 g, 5.55 mmol, 88% yield) as a colorless to light yellow oil. lc/ms m/z 234 [M + H]+.

References

[1] Patent: WO2012/75383, 2012, A2. Location in patent: Page/Page column 82
[2] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 9, p. 835 - 840
[3] Patent: WO2013/184878, 2013, A1. Location in patent: Paragraph 00241; 00242
[4] Patent: WO2013/184876, 2013, A1. Location in patent: Paragraph 00144; 00147; 00148
[5] Patent: WO2016/97870, 2016, A1. Location in patent: Paragraph 0168