Chloromethyl Methyl Ether → 1-Bromo-2,3-bis(methoxymethyloxy)-4-methoxy-benzene

Participants

Reaction Steps

To a solution of 1-bromo-2,3-dihydroxy-4-methoxy-benzene (5.0 g) and anhydrous tetrahydrofuran (20 mL) at 0° C. under argon was added diisopropylethylamine (8.0 mL). The solution was stirred for 15 min, methyloxymethyl chloride (3.5 mL) was added, and the reaction mixture stirred for 3 hours. The solution was poured into water (250 mL), extracted with dichloromethane and the solvent removed in vacuo to provide an orange oil. The oil was purified by flash column chromatography (hexane-ethyl acetate, 2:1) to yield a clear oil (6.4 g, 91%): EIMS m/z 308 (M+, 81Br), 306 (M+, 79Br), 232, 230, 45; IR (neat, cm−1) vmax 2963, 2836, 1221, 1159, 1084, 966; 1H NMR δ 7.25 (1H, d, J=9.0 Hz, H5), 6.61 (1H, d, J=9.0 Hz, H4), 5.20 (2H, s, OCH2), 5.13 (2H, s, OCH2), 3.84 (3H, s, OCH3), 3.66 (3H, s, OCH3), 3.59 (3H, s, OCH3); 13C—NMR (75.5 MHZ) δ 153.31, 148.24, 140.05, 127.49, 108.94, 108.73, 99.39, 98.73, 58.14, 57.46, 56.11. Anal. Calcd. For C11H15O5Br: C, 43.02; H, 4.92. Found: C, 42.86; H, 4.93.

Provenance & Evidence