Iodoethane → 2-Bromo-5-[(ethyloxy)methyl]furan

Temperature

0 °C

Sodium hydride (95%, 19 mg, 0.75 mmol) was diluted in dry DMF (0.5 mL) and cooled to 0° C. A solution of (5-bromo-2-furanyl)methanol (120 mg, 0.68 mmol) was added, and the mixture was stirred for 5 minutes. Ethyl iodide (117 mg, 0.75 mmol) was added, and the mixture was stirred at it overnight. The reaction mixtures were quenched by the careful addition of water, then extracted with diethyl ether. The combined organics were dried and concentrated. The residue was purified by flash chromatography, eluting with 10% EtOAc/hexanes. The desired fractions were combined and concentrated to afford the title compound.

1. stirringthe mixture was stirred at it overnight
2. customThe reaction mixtures
3. customwere quenched by the careful addition of water
4. extractionextracted with diethyl ether
5. customThe combined organics were dried
6. concentrationconcentrated
7. customThe residue was purified by flash chromatography
8. washeluting with 10% EtOAc/hexanes
9. concentrationconcentrated

ORD record

ord-8549bd640e984336ab3297e886e98be6

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08372875B2