2-Bromo-2-(2-fluorophenyl)-1-cyclopropylethanone Chemical Properties

Boiling point:

293.0±25.0 °C(Predicted)

Density 

1.574±0.06 g/cm3(Predicted)

Flash point:

131°

storage temp. 

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

solubility 

Chloroform (Sparingly), Ethyl Acetate (Slightly)

form 

Oil to Low-Melting Solid

form 

Oil to Low-Melting Solid

color 

Yellow to Light Brown

optical activity

0.0900°(C=1g/100mL, CHCL3, 20°C, 589nm)

CAS DataBase Reference

204205-33-4(CAS DataBase Reference)

Safety Information

HS Code 

2914.79.4000

2-Bromo-2-(2-fluorophenyl)-1-cyclopropylethanone Usage And Synthesis

Uses

2-?Bromo-?2-?(2-?fluorophenyl)?-?1-?cyclopropylethanone is a reagent used in the synthesis of potent anti-oxidant agents.

Synthesis

General procedure for the synthesis of 2-bromo-2-(2-fluorophenyl)-1-cyclopropylethanone from 1-cyclopropyl-2-(2-fluorophenyl)ethanone: 1-cyclopropyl-2-(2-fluorophenyl)ethanone (17.8 g, 100 mmol), iodine monobromide (62 g, 300 mmol), and 1-butyl-3-methylimidazolium bromide (8.7 g, 40 mmol) were dissolved in 150 mL of anhydrous tetrahydrofuran. The reaction was stirred at 40 °C for 4 hours. After completion of the reaction, the mixture was cooled to room temperature and the reaction was quenched by the addition of ice water. The reaction mixture was extracted with ethyl acetate and the organic phase was washed with saturated sodium bisulfite solution. The organic phase was concentrated and purified by recrystallization from ethanol to give 2-bromo-2-(2-fluorophenyl)-1-cyclopropylethanone (24.5 g, 95.3% yield, 99.73% purity).

References

[1] Patent: CN105884793, 2016, A. Location in patent: Paragraph 0033; 0034; 0035
[2] Patent: WO2013/14295, 2013, A1. Location in patent: Page/Page column 19-20
[3] Patent: WO2009/122440, 2009, A1. Location in patent: Page/Page column 31
[4] Patent: CN105884599, 2016, A. Location in patent: Paragraph 0025; 0062-0064
[5] Patent: CN104418718, 2018, B. Location in patent: Paragraph 0040; 0044; 0047; 0048; 0052; 0056

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