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

Participants

Reaction Steps

To a solution of 2-Bromo-6-methoxy-3-propyl-naphthalen-1-ol (94) (1.41 g, 4.78 mmol) in dry THF (23 mL) at 0° C. was added diisopropylethylamine (3.3 mL, 19.1 mmol) followed by chloromethyl methyl ether (1.1 mL, 14.3 mmol) slowly. Reaction mixture was stirred at ambient temperature for 24 h. Reaction mixture was diluted with water and the aqueous layer was extracted with DCM, washed organic layer with brine, dried over Na2SO4, filtered and concentrated. The crude material was purified using 1:9 EtOAc:hexanes to provide 1.26 g (78%) of the title compound (95) as a solid. 1H NMR (400 MHz, d-CDCl3): δ 1.01 (t, J=7.4 Hz, 3H), 1.70-1.75 (m, 2H), 2.85 (t, J=7.7 Hz, 2H), 3.72 (s, 3H), 3.91 (s, 3H), 5.23 (s, 2H), 7.04 (s, 1H), 7.12 (dd, J1=2.6 Hz, J2=9.1 Hz, 1H), 7.39 (s, 1H), 8.03 (d, J=9.1 Hz, 1H).

Provenance & Evidence