(3-Methoxyphenyl)boronic acid → 3-(3-Methoxyphenyl)cyclohex-2-enone

Participants

Reaction Steps

Synthesized from 3-bromocyclohex-2-enone and 3-methoxyphenylboronic acid according to the general procedure described for the Suzuki coupling. Purification by automated flash chromatography using gradient elution (0 to 80% ethyl acetate/hexanes) yielded the product (141 mg, 88%) as a pale yellow solid. 1H NMR (300 MHz, CDCl3): δ 7.30 (t, J=8.0 Hz, 1H), 7.10 (dd, J=8.0, 0.8 Hz, 1H), 7.03 (t, J=2.2 Hz, 1H), 6.93 (dd, J=8.3, 2.5 Hz, 1H), 6.39 (bs, 1H), 3.82 (s, 3H), 2.75 (td, J=6.1, 0.8 Hz, 2H), 2.48 (t, J=6.3 Hz, 2H), 2.14 (quintet, J=6.1 Hz, 2H).

Provenance & Evidence