5-Bromo-2-furaldehyde

Chemical Properties

solid

Physical properties

5-Bromo-2-furfuraldehyde is a light yellow powder, soluble in carbon dichloride , carbon tetrachloride, ether and other organic solvents.

Uses

5-Bromo-2-furaldehyde is used in the preparation of isoindolinones from furfural. Also used in the preparation of brominated nitrovinylfuran which displays antibacterial activity.

Uses

5-Bromo-2-furaldehyde may be employed for the following syntheses:

• 5-substituted 2-furaldehydes
• anilines, through a novel one-pot, two-step amination/Diels-Alder procedure
• 5-(5′,8′-dimethyl-9′-tert-butoxycarbonyl-9′H-carbazol-3′-yl)-furan-2-carbaldehyde
• 5-(6-hydroxyhexyl)-2-furaldehyde
• 5-methylsulfonyl-2-furaldehyde
• 5-phenylsulfonyl-2-furaldehyde
• 5-(4-acetamidobenzylsulfonyl)-2-furaldehyde
• 5-iodo-2-furaldehyde

Preparation

A three-necked 50 mL round bottom flask was charged with [bmim]Br3 (20 mmol) followed by dropwise addition of freshly distilled 2-furfural (20 mmol) over a period of 0.5 h and the reaction mixture was stirred for at 40 ℃ 2.5 h under nitrogen atmosphere. The mixture was extracted with petroleum ether (30 mL × 3), the organic layer was washed with water, dried (sodium sulfate) and concentrated. The crude product was purified by distillation and recrystallization with 10 % ethyl acetate-ether solution.
5-Bromo-2-furfural of yellowish crystal in 88 % yield was obtained. Mp. 82-85 ℃, 1H NMR (CDCl3), δ: 9.55 (s, 1H), 7.25 (s, 1H), 6.57 (s, 1H).