Methyl iodide → 2-Bromo-5-[(methyloxy)methyl]furan

Sodium hydride (95%, 28 mg, 1.12 mmol) was diluted in dry DMF (1 mL) and cooled to 0° C. (5-bromo-2-furanyl)methanol (177 mg, 1 mmol) in DMF (2 mL) was added, and the mixture was stirred for 5 minutes. Methyl iodide (0.07 mL, 1.12 mmol) was added, and the mixture was stirred at room temperature overnight. The reaction mixture was quenched by the careful addition of water, then extracted with ethyl acetate (20 mL), followed by dichloromethane (20 mL). The combined organics were dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography, eluting with EtOAc/hexanes. The desired fractions were combined and concentrated, giving 40 mg (21%) of the title compound.

1. additionwas added
2. stirringthe mixture was stirred at room temperature overnight
3. customThe reaction mixture was quenched by the careful addition of water
4. extractionextracted with ethyl acetate (20 mL)
5. dry with materialThe combined organics were dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified by flash chromatography
9. washeluting with EtOAc/hexanes
10. concentrationconcentrated

ORD record

ord-d91206e437e94c6d96f3bcbc9150a1bd

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08071584B2