2'-BROMO-5'-FLUOROACETOPHENONE Chemical Properties

Boiling point:

144℃/18mm

Density 

1.535±0.06 g/cm3(Predicted)

refractive index 

1.5525

storage temp. 

Sealed in dry,Room Temperature

solubility 

Soluble in methanol.

form 

liquid

color 

Clear, pale lemon/lime

Safety Information

HS Code 

2914790090

2'-BROMO-5'-FLUOROACETOPHENONE Usage And Synthesis

Uses

2'-Bromo-5'-fluoroacetophenone is used in the synthesis of oxabicyclic compounds. It is also used in the enantioselective synthesis of chiral 3-aryl-1-indanone molecules.

Synthesis

General procedure for the synthesis of 2-bromo-5-fluoroacetophenone from 1-(2-bromo-5-fluorophenyl)ethanol: 1. Preparation of 1-(2-bromo-5-fluorophenyl)ethanone Trichloroisocyanuric acid (59.5 g, 0.256 mol, 1.05 eq.) was added to a solution of 1-(2-bromo-5-fluorophenyl)ethanol (53.4 g, 0.2438 mol) in dichloromethane (500 mL) at 0-20 °C. To the resulting suspension was added TEMPO (2,2,6,6-tetramethylpiperidine 1-yloxy; 188 mg, 1.20 mmol, 0.5 mol%). The reaction mixture was stirred at ice bath temperature until the oxidation was complete (HPLC monitoring, about 4.5 hours). The reaction mixture was diluted with methyl tert-butyl ether (MTBE, ca. 1300 mL), sequentially with 1N NaOH (2 × 250 mL), 1N HCl containing potassium iodide (for the removal of TEMPO; 8 g of KI in 1000 mL of 1N HCl; 2 × 250 mL), 1N NaHCO3 containing sodium thiosulfate (for the removal of I2; 15 g Na2S2O3 in 1000 mL of 1N NaHCO3), 1N HCl containing potassium iodide (1 × 200 mL), 1N NaHCO3 containing sodium thiosulfate (2 × 200 mL), and brine (150 mL) washed. After drying (anhydrous MgSO4), the solvent was removed under reduced pressure to give 1-(2-bromo-5-fluorophenyl)ethanone as a light amber liquid (52.96 g, about 97% yield) with 98% purity by HPLC, which can be used in the next reaction without further purification. 1H-NMR (300MHz, CDCl3) δ 7.59 (dd, J=8.7,4.9Hz, 1H), 7.19 (dd, J=8.5,3.0Hz, 1H), 7.04 (ddd, J=9.1,7.8,3.0Hz, 1H), 2.64 (s, 3H).

References

[1] Patent: WO2010/111418, 2010, A2. Location in patent: Page/Page column 99
[2] Organic and Biomolecular Chemistry, 2011, vol. 9, # 22, p. 7836 - 7848
[3] Journal of Organic Chemistry, 2017, vol. 82, # 21, p. 11585 - 11593
[4] Organic Letters, 2012, vol. 14, # 12, p. 3230 - 3232
[5] Journal of the American Chemical Society, 2014, vol. 136, # 48, p. 16748 - 16751

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