Methyl iodide → 1-Bromo-2-methoxynaphthalene

1-Bromo-2-naphthol (2.0 g, 8.97 mmol) was dissolved in THF (20 mL), and the solution was cooled to 0 deg in an ice bath. NaH was added thereto (60% dispersion of in mineral oil, 430 mg 10.8 mmol), followed by MeI (1.2 mL, 19.6 mmol) as bubbling subsided. The reaction mixture was heated to reflux overnight, cooled to room temperature, and water added dropwise thereto until bubbling subsided. The reaction mixture was diluted with EtOAc, and the organic layer was washed once each with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 10% to 50% EtOAc/hexanes to afford 1-bromo-2-methoxynaphthalene as a solid. LC/MS (ES MS, M+H+ found: 238) and proton NMR (400 MHz, CDCl3) δ 4.04 (s, 3H), 7.28 (d, J=9 Hz, 1H), 7.42 (t, J=7 Hz, 1H), 7.58 (t, J=6.8 Hz, 1H), 7.8 (dd, J=9 Hz, 2H), 8.2 (d, J=8.6 Hz, 1H).

1. temperaturethe solution was cooled to 0 deg in an ice bath
2. customas bubbling
3. temperatureThe reaction mixture was heated
4. temperatureto reflux overnight
5. additionwater added dropwise
6. customuntil bubbling
7. additionThe reaction mixture was diluted with EtOAc
8. washthe organic layer was washed once each with water and brine
9. dry with materialdried over sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure
12. customThe residue was purified by silica gel chromatography
13. washeluting with 10% to 50% EtOAc/hexanes

ORD record

ord-672a06ec8784432db3a407b31e338d10

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07332499B2