p-Toluenesulfonic acid monohydrate → HCID 10826647, compound

Participants

Reaction Steps

To a solution of methyl 3-bromo-5-hydroxy-6,7,8,9-tetrahydro-5H-benzo[7]annulene-6-carboxylate from step A3 (230 mg, 0.769 mmol) in toluene (3 mL) was added p-toluenesulfonic acid monohydrate (29.2 mg, 0.154 mmol). The mixture was heated at reflux for 4 h. The solvent was removed in vacuo, and the residue was purified using silica gel column chromatography (hexanes-10% EtOAc) to give methyl 2-bromo-6,7-dihydro-5H-benzo[7]annulene-8-carboxylate (175 mg, 0.622 mmol, 81% yield). 1H NMR (500 MHz, chloroform-d) δ 7.61 (s, 1H), 7.44 (d, J=1.8 Hz, 1H), 7.32 (dd, J=8.1, 2.0 Hz, 1H), 7.02 (d, J=7.9 Hz, 1H), 3.83 (s, 3H), 2.79-2.72 (m, 2H), 2.63 (t, J=6.6 Hz, 2H), 2.09-2.00 (m, 2H).

Provenance & Evidence