Sulfuryl chloride → 4-Chloro-4-(4'-chloro-4-methylbiphenyl-3-yl)-2,2,6,6-tetramethyl-pyran-3,5-dione
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([CH:15]3[C:20](=[O:21])[C:19]([CH3:23])([CH3:22])[O:18][C:17]([CH3:25])([CH3:24])[C:16]3=[O:26])[CH:9]=2)=[CH:4][CH:3]=1.S(Cl)([Cl:30])(=O)=O>C(Cl)(Cl)Cl>[Cl:30][C:15]1([C:10]2[CH:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH:13]=[CH:12][C:11]=2[CH3:14])[C:20](=[O:21])[C:19]([CH3:22])([CH3:23])[O:18][C:17]([CH3:25])([CH3:24])[C:16]1=[O:26]Participants
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 4-(4′-chloro-4-methylbiphenyl-3-yl)-2,2,6,6-tetramethylpyran-3,5-dione in anhydrous chloroform (3 ml) at 0° C. is added a second solution of sulfuryl chloride (0.025 ml, 0.315 mmol) in anhydrous chloroform (0.3 ml) dropwise. The reaction mixture is stirred for 30 minutes at 0° C. then for a further 1 hour at room temperature. Additional sulfuryl chloride (0.025 ml, 0.315 mmol) is next added, followed by warming to 60° C. for 2 hours, followed by addition of further sulfuryl chloride (0.20 ml, 2.52 mmol). The reaction mixture is finally stirred at room temperature overnight then quenched with saturated aqueous sodium bicarbonate, and extracted with ethylacetate. Purification by flash column chromatography (20% ethylacetate in hexane eluant) afforded 4-chloro-4-(4′-chloro-4-methylbiphenyl-3-yl)-2,2,6,6-tetramethyl-pyran-3,5-dione (0.033 g) as a yellow oil.
Workup
- waitfor a further 1 hour at room temperature
- temperatureby warming to 60° C. for 2 hours
- stirringThe reaction mixture is finally stirred at room temperature overnight
- customthen quenched with saturated aqueous sodium bicarbonate
- extractionextracted with ethylacetate
- customPurification by flash column chromatography (20% ethylacetate in hexane eluant)
Sources & evidence
- ORD record
- ord-3cbad54913c544d983f3b273f8e03832
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08623907B2
Reaction notes
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