7-BROMO-2,3-DIHYDRO-1-BENZOFURAN Chemical Properties

Boiling point:

254.4±29.0 °C(Predicted)

Density 

1.582±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

Appearance

White to light yellow Solid

Safety Information

HS Code 

2932990090

7-BROMO-2,3-DIHYDRO-1-BENZOFURAN Usage And Synthesis

Synthesis

Synthesis of 7-bromo-2,3-dihydrobenzofuran: In a dry reaction flask, 1,3-dibromo-2-(2-bromoethoxy)benzene (11.5 g, 32.0 mmol) was dissolved in a mixed solvent of 115 mL of anhydrous THF and 28 mL of hexane. The reaction system was cooled to -78 °C under nitrogen protection, and 2.5 M n-butyllithium (n-BuLi, 13.0 mL, 32.5 mmol) solution was slowly added dropwise for a controlled time of 30 min. After the dropwise addition was completed, the reaction was kept at -78 °C for 30 min and then the reaction system was slowly warmed up to 0 °C. After completion of the reaction, the mixture was carefully poured into 100 mL of ice water and the aqueous phase was extracted with ether (3 x 50 mL). The organic layers were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to give a light yellow oily crude product. The crude product was purified by silica gel column chromatography with gradient elution of ethyl acetate/hexane to afford colorless needle-like crystals of 7-bromo-2,3-dihydrobenzofuran (5.00 g, 78% yield). The structure of the product was confirmed by 1H NMR (500 MHz, DMSO-d6): δ 7.27 (dd, J=1,8Hz, 1H), 7.20 (dd, J=1,7.5Hz, 1H), 6.75 (t, J=7.8Hz, 1H), 4.59 (t, J=9Hz, 2H), 3.28 (t, J=8.8Hz, 2H).

References

[1] Tetrahedron Letters, 1998, vol. 39, # 15, p. 2219 - 2222
[2] Patent: US2006/30583, 2006, A1. Location in patent: Page/Page column 104
[3] Patent: EP1972628, 2008, A1. Location in patent: Page/Page column 56-57
[4] Patent: US2010/16297, 2010, A1. Location in patent: Page/Page column 34

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