Sulfuryl chloride → 4-Chloro-4-(2',4'-dichloro-4-ethylbiphen-3-yl)-2,2,6,6-tetramethylpyran-3,5-dione

HRID 468207Notes

Reaction equation

HRID 468207 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[C:11]([CH:17]2[C:22](=[O:23])[C:21]([CH3:25])([CH3:24])[O:20][C:19]([CH3:27])([CH3:26])[C:18]2=[O:28])[CH:10]=1.S(Cl)([Cl:32])(=O)=O>C(Cl)(Cl)Cl>[Cl:32][C:17]1([C:11]2[CH:10]=[C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])[CH:14]=[CH:13][C:12]=2[CH2:15][CH3:16])[C:22](=[O:23])[C:21]([CH3:25])([CH3:24])[O:20][C:19]([CH3:27])([CH3:26])[C:18]1=[O:28]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 668235414-(2',4'-Dichloro-4-ethylbiphenyl-3-yl)-2,2,6,6-tetramethylpyran-3,5-dione

Product 1

HCID 583124284-Chloro-4-(2',4'-dichloro-4-ethylbiphen-3-yl)-2,2,6,6-tetramethylpyran-3,5-dioneYield 96.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4-(2′,4′-dichloro-4-ethylbiphenyl-3-yl)-2,2,6,6-tetramethylpyran-3,5-dione (0.220 g, 0.525 mmol) in dry chloroform (4 ml) is added sulfuryl chloride (0.085 ml, 1.05 mmol), followed by stirring at room temperature for 4 hours. After dilution with diethyl ether (150 ml) the organic phase is washed with saturated sodium carbonate (150 ml) then dried over magnesium sulphate and the filtrate concentrated in vacuo to afford 4-chloro-4-(2′,4′-dichloro-4-ethylbiphen-3-yl)-2,2,6,6-tetramethylpyran-3,5-dione (0.229 g, 96%) as a white solid.

Workup

  1. washAfter dilution with diethyl ether (150 ml) the organic phase is washed with saturated sodium carbonate (150 ml)
  2. dry with materialthen dried over magnesium sulphate
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-12c63cc25d6c4aacad3b21d3c8a45fab
Source dataset
uspto-grants-2014_01
Patent number
US08623907B2

Reaction notes

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