1-Ethynyl-4-methoxybenzene → 1-(3,5-Dichlorophenyl)-3-(4-methoxyphenyl)prop-2-yn-1-one

HRID 2102234Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[CH:10])=[CH:5][CH:4]=1.C([Li])CCC.[Cl:16][C:17]1[CH:18]=[C:19]([CH:26]=[C:27]([Cl:29])[CH:28]=1)[C:20](N(OC)C)=[O:21]>C1COCC1>[Cl:16][C:17]1[CH:18]=[C:19]([C:20](=[O:21])[C:10]#[C:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:26]=[C:27]([Cl:29])[CH:28]=1

Participants

Conditions

Temperature: -40 °C

Procedure

To a solution of 4-methoxy-1-ethynyl benzene (0.57 g, 4.27 mmol) in 20 mL of anhydrous THF cooled to −78° C. under a N2 atmosphere was added nButLi (3.2 mL, 5.12 mmol). After 5 minutes a solution of 3,5-dichloro-N-methoxy-N-methylbenzamide (1.0 g, 4.27 mmol) in THF (10 mL) was added to the reaction. The reaction was slowly warmed to −40° C. over 30 minutes and then quenched with saturated NH4Cl solution. The resulting bi-phasic mixture was extracted with EtOAc (3×). The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography using 1:10 ethyl acetate-hexanes to give the title compound as a yellow solid. 1H NMR (CDCl3, 500 MHz): δ 8.09(d, J=2.0 Hz, 2H), 7.7(d, J=7.1 Hz, 2H), 7.64(t, J=1.8 Hz, 1H), 7.0(d, J=8.7 Hz, 1H), 3.91(s, 3H).

Workup

customquenched with saturated NH4Cl solution
extractionThe resulting bi-phasic mixture was extracted with EtOAc (3×)
washThe organic layer was washed with brine
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-b59970469dac4b32ad7288d91100a9e8
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572922B2

Reaction notes

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