Chloromethyl Methyl Ether → 2-Bromo-6-methoxy-1-methoxymethoxy-3-propyl-naphthalene

Participants

Reaction Steps

2-Bromo-6-(methyloxy)-3-propyl-1-naphthalenol (94) (0.62 g, 2.10 mmol) was treated with chloromethyl methyl ether in the presence of diisopropylethylamine in THF to give 0.66 g (92%) of the title compound (95) as a light yellow oil. 1H NMR (400 MHz, CDCl3): δ 1.02 (t, J=7.3 Hz, 3H), 1.65-1.75 (m, 2H), 2.84 (t, J=7.7 Hz, 2H), 3.72 (s, 3H), 3.90 (s, 3H), 5.23 (s, 2H), 7.04 (d, J=2.6 Hz, 1H), 7.12 (dd, J1=9.3 Hz, J2=2.5 Hz, 1H), 7.38 (s, 1H), 8.03 (d, J=9.1 Hz, 1H). LCMS (ESI): m/z 361 (M+Na)+, m/z 337 (M−H)−.

Provenance & Evidence