Dibenzofuran-4-boronic acid → 3-Dibenzofuran-4-yl-cyclohex-2-enone

HRID 1675501Notes

Reaction equation

HRID 1675501 reaction equation
Br[C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=1.[CH:9]1[C:17]2[C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[O:14][C:13]=2[C:12](B(O)O)=[CH:11][CH:10]=1>>[CH:9]1[C:17]2[C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[O:14][C:13]=2[C:12]([C:2]2[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=2)=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 2734328Dibenzofuran-4-boronic acidHCID 109650383-Bromocyclohex-2-enone

Product 1

HCID 247473083-Dibenzofuran-4-yl-cyclohex-2-enoneYield 83%

Procedure

Synthesized from 3-bromocyclohex-2-enone and dibenzofuran-4-boronic acid according to the general procedure described for the Suzuki coupling. Purification by automated flash chromatography using gradient elution (0 to 20% ethyl acetate/hexanes) yielded the product (141 mg, 83%) as a white solid. 1H NMR (300 MHz, CDCl3): δ 7.91 (d, J=6.9 Hz, 2H), 7.30-7.58 (m, 5H), 6.90 (s, 1H), 2.97 (t, J=4.7 Hz, 2H), 2.56 (t, J=6.1 Hz, 2H), 2.21 (quintet, J=5.8 Hz, 2H). 13C (75 MHz, CDCl3): 200.1, 156.2, 155.9, 153.3, 128.6, 127.7, 125.6, 125.3, 124.0, 123.5, 123.2, 123.0, 122.0, 120.7, 111.9, 37.7, 29.0, 23.2. HRMS (LCT Electrospray): mass calcd for (C18H14O2+Na) m/z 285.0891; measured [M+Na]+: m/z 285.0895.

Workup

  1. customPurification by automated flash chromatography
  2. washelution (0 to 20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-b4fcb3f0cd904cfa90d8e05c9abe5b5d
Source dataset
uspto-grants-2011_08
Patent number
US08003692B2

Reaction notes

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