6-Bromobenzofuran Chemical Properties

Boiling point:

234℃

Density 

1.608

Flash point:

95℃

storage temp. 

2-8°C

solubility 

Chloroform, Dichloromethane, Ethyl Acetate

form 

Oil

color 

Light Yellow

Stability:

Volatile

InChI

InChI=1S/C8H5BrO/c9-7-2-1-6-3-4-10-8(6)5-7/h1-5H

InChIKey

BBXQYOQXGGJUFK-UHFFFAOYSA-N

SMILES

O1C2=CC(Br)=CC=C2C=C1

Safety Information

HS Code 

2932990090

6-Bromobenzofuran Usage And Synthesis

Chemical Properties

Light Yellow Oil

Synthesis

Polyphosphoric acid (PPA, 0.743 g, 6.83 mmol) was added to a solution of compound 175 (0.656 g, 2.28 mmol) in toluene (4.6 mL) under an argon atmosphere and stirred at room temperature. The reaction mixture was heated to reflux and maintained for 4 hours. Upon completion of the reaction, it was cooled to room temperature and the reaction was quenched with ice water and subsequently extracted with ethyl acetate (EtOAc). The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure. The crude products were purified by silica gel column chromatography (eluent: ethyl acetate/hexane, 2:98) to afford 6-bromobenzofuran (176, main product, 0.206 g, 1.05 mmol, 46% yield) and 4-bromobenzofuran (177, by-product, 0.183 g, 0.935 mmol, 41% yield, colorless oily substance), respectively. 1H-NMR (CDCl3, 400 MHz) data for 6-bromobenzofuran (176): δ 6.75 (d, J = 1.6 Hz, 1H, furan-H), 7.36 (dd, J = 1.2, 8.4 Hz, 1H, Ar-H), 7.46 (d, J = 8.4 Hz, 1H, Ar-H), 7.60 (d, J = 1.6 Hz 1H, furan-H), 7.69 (s, 1H, Ar-H). 1H-NMR (CDCl3, 400 MHz) data for 4-bromobenzofuran (177): δ 6.82 (d, J = 2.4 Hz, 1H, furan-H), 7.17 (dd, J = 7.6, 8.4 Hz, 1H, Ar-H), 7.40 (d, J = 7.6 Hz, 1H, Ar-H), 7.45 (d, J = 8.4 Hz 1H, Ar-H), 7.66 (d, J = 2.4 Hz, 1H, furan-H).

References

[1] Phytochemistry, 2013, vol. 96, p. 132 - 147
[2] Patent: US7045545, 2006, B1. Location in patent: Page/Page column 20
[3] Patent: EP1204659, 2003, B1. Location in patent: Page/Page column 15-16
[4] Journal of Medicinal Chemistry, 1997, vol. 40, # 3, p. 322 - 330
[5] Tetrahedron, 2015, vol. 71, # 29, p. 4835 - 4841

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