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

HRID 1675518Notes

Reaction equation

HRID 1675518 reaction equation
Br[C:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4](=[O:10])[CH:3]=1.[CH:11]1[C:19]2[C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[O:16][C:15]=2[C:14](B(O)O)=[CH:13][CH:12]=1>>[CH:11]1[C:19]2[C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[O:16][C:15]=2[C:14]([C:2]2[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4](=[O:10])[CH:3]=2)=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 1394173-Bromo-5,5-dimethyl-2-cyclohexen-1-oneHCID 2734328Dibenzofuran-4-boronic acid

Product 1

HCID 24747309HCID 24747309, compoundYield 96%

Procedure

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.

Workup

  1. customPurification by automated flash chromatography

Sources & evidence

ORD record
ord-20f2874c11ff49ccaa93a5694430a156
Source dataset
uspto-grants-2011_08
Patent number
US08003692B2

Reaction notes

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