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

HRID 1675509Notes

Reaction equation

HRID 1675509 reaction equation
Br[C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=1.[CH3:9][O:10][C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][CH:16]=1>>[CH3:9][O:10][C:11]1[CH:12]=[C:13]([C:2]2[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=2)[CH:14]=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 2734370(3-Methoxyphenyl)boronic acidHCID 109650383-Bromocyclohex-2-enone

Product 1

HCID 114583403-(3-Methoxyphenyl)cyclohex-2-enoneYield 88%

Procedure

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).

Workup

  1. customPurification by automated flash chromatography
  2. washelution (0 to 80% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-a5cb94415ae34c7184036614ff85548c
Source dataset
uspto-grants-2011_08
Patent number
US08003692B2

Reaction notes

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