3-Bromo-5,5-dimethyl-2-cyclohexen-1-one → HCID 24747309, compound

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Reaction Steps

Synthesized from 3-bromo-5,5-dimethylcyclohex-2-enon and dibenzofuran-4-boronic acid according to the general procedure described for the Suzuki coupling. Purification by automated flash chromatography yielded the product (192 mg, 96%) as a white solid. 1H NMR (300 MHz, CDCl3): δ 7.93 (dd, J=7.4, 1.1 Hz, 1H), 7.92 (ddd, J=7.7, 0.8, 0.6 Hz, 1H), 7.59 (d, J=8.3 Hz, 1H), 7.51-7.43 (m, 2H), 7.34 (t, J=7.7 Hz, 1H), 7.33 (t, J=7.4 Hz, 1H), 6.91 (t, J=1.4 Hz, 1H), 2.85 (d, J=1.4 Hz, 2H), 2.42 (s, 2H), 1.19 (s, 6H). 13C (75 MHz, CDCl3): δ 200.3, 156.0, 153.9, 153.4, 127.7, 127.6, 125.6, 125.3, 124.3, 123.6, 123.2, 123.0, 122.0, 120.7, 112.0, 51.3, 43.0, 34.2, 28.7. HRMS (LCT Electrospray): mass calcd for (C20H18O2+Na) m/z 313.1204; measured [M+Na]+: m/z 313.1201.

Provenance & Evidence