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

HRID 1675519Notes

Reaction equation

HRID 1675519 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:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O>>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=1

Participants

3

Reactant 2

HCID 27339582-Methoxyphenylboronic acidHCID 109650383-Bromocyclohex-2-enone

Product 1

HCID 123391193-(2-Methoxyphenyl)cyclohex-2-enoneYield 98%

Procedure

Synthesized from 3-bromocyclohex-2-enone and 2-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 (166 mg, 98%) as a pale yellow oil. 1H NMR (300 MHz, CDCl3): δ 7.32 (ddd, J=8.3, 7.4, 1.9 Hz, 1H), 7.18 (dd, J=7.7, 1.9 Hz, 1H), 6.96 (dd, J=7.4, 1.1 Hz, 1H), 6.91 (d, J=8.5 Hz, 1H), 6.18 (t, J=1.8 Hz, 1H), 3.83 (s, 3H), 2.73 (td, J=6.1, 1.4 Hz, 2H), 2.48 (t, J=6.3 Hz, 2H), 2.14-2.06 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-7fa7cbcf7f1a44fd9d3dbe601e06bcb8
Source dataset
uspto-grants-2011_08
Patent number
US08003692B2

Reaction notes

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