Bromine → 3-Bromo-6-methoxy-2-(4-methoxyphenyl)-benzo[b]thiophene

Participants

Reaction Steps

To a solution of 6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene (27.0 g, 100 mmol)in 1.10 L of CHCl3 at 60° C. was added bromine (15.98 g, 100 mmol) dropwise as a solution in 200 mL of CHCl3. After the addition was complete, the reaction was cooled to room temperature, and the solvent removed in vacuo to provide 34.2 g (100%) of 6-methoxy-2-(4-methoxyphenyl)-3-bromobenzo[b]thiophene as a white solid. mp 83-85 OC. 1H NMR (DMSO-d6) δ 7.70-7.62 (m, 4H), 7.17 (dd, J=8.6, 2.0 Hz, 1H), 7.09 (d, J=8.4 Hz, 2H). FD mass spec: 349, 350. Anal. Calcd. for C16H13O2SBr: C, 55.03; H, 3.75. Found: C, 54.79; H, 3.76.

Provenance & Evidence