Pyridine → 1-(4-Chlorophenyl)-2-(2,4-dichlorophenyl)ethane-1,2-dione

HRID 1392124

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])=[O:10])=[CH:4][CH:3]=1.C1C=C[NH+]=CC=1.[O-:25][Cr](Cl)(=O)=O.N1C=CC=CC=1>ClCCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:25])[C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])=[O:10])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

2-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)ethanone (2.7 g, 9.01 mmol) was dissolved in 1,2-dichloroethane (25 ml) and freshly made PCC (3.89 g, 18.02 mmol), pyridine (1.43 g, 18.02 mmol) and molecular sieves were added. The reaction mixture was refluxed under inert atmosphere overnight. The solution was cooled to 25° C., filtered through Silica and then solvent was evaporated under reduced pressure. The crude product (1.9 g, 66%) was used directly in the next step. 1H NMR (500 MHz) δ 7.97 (d, 2H), 7.84 (d, 1H), 7.52 (d, 2H), 7.46 (s, 1H), 7.44 (d, 1H).

Workup

temperatureThe reaction mixture was refluxed under inert atmosphere overnight
filtrationfiltered through Silica
customsolvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-3cbb9601a1ed43258aaa8f322aa5f853
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07342019B2

Linked notes

Loading…