5-Bromo-2,3-dihydro-1-benzofuran Chemical Properties

Melting point:

49 °C

Boiling point:

251.7±29.0 °C(Predicted)

Density 

1.582±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

color 

White to Light yellow

CAS DataBase Reference

66826-78-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-52-22

Safety Statements 

26-36/37/39-37/39

HS Code 

2932990090

5-Bromo-2,3-dihydro-1-benzofuran Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

5-Bromo-2,3-dihydrobenzofuran, is an organic building block that can be used in the synthesis of Darifenacin (D193400), a drug used to treat urinary incontinence.

Synthesis

General procedure for the synthesis of 5-bromo-2,3-dihydrobenzofuran from 2,3-dihydrobenzofuran: Liquid bromine (2.66 g) was added slowly and dropwise to dioxane (30 mL) under cooling conditions in an ice bath and stirred for 30 min at this temperature. Subsequently, 2,3-dihydrobenzofuran (2 g) was added dropwise to the reaction mixture and stirring was continued for 3 hours at room temperature. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was dissolved in ethyl acetate (50 mL), washed sequentially with saturated aqueous sodium bicarbonate and brine, and dried over anhydrous magnesium sulfate. The solvent was removed by evaporation to give an orange oily crude product. The crude product was purified by silica gel column chromatography (eluent: hexane-ethyl acetate, 20:1) to afford 2.33 g of 5-bromo-2,3-dihydrobenzofuran white crystals in 70.3% yield. The product was characterized by 1H-NMR (300 MHz, CDCl3, δ): 3.11 (2H, t, J = 11 Hz), 4.57 (2H, t, J = 11 Hz), 6.66 (1H, d, J = 8 Hz), 7.20 (1H, d, J = 8 Hz), 7.30 (1H, s).

References

[1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 16, p. 4313 - 4336
[2] Chemistry - A European Journal, 2017, vol. 23, # 5, p. 1044 - 1047
[3] Synthesis, 1988, # 12, p. 950 - 952
[4] Patent: US6333324, 2001, B1
[5] Patent: WO2003/82787, 2003, A1. Location in patent: Page/Page column 137-138

5-Bromo-2,3-dihydro-1-benzofuran(66826-78-6)Related Product Information

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