Hydrochloric Acid → 4-[2-Ethyl-5-(3-fluorophenoxy)phenyl]-2,2,6,6-tetramethylpyran-3,5-dione

HRID 537677Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:20][CH3:21])=[C:6]([CH:8]2[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[O:11][C:10]([CH3:18])([CH3:17])[C:9]2=[O:19])[CH:7]=1.[F:22][C:23]1[CH:24]=[C:25]([OH:29])[CH:26]=[CH:27][CH:28]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>C1(C)C=CC=CC=1.ClCCl.FC(F)(F)S([O-])(=O)=O.[Cu+2].FC(F)(F)S([O-])(=O)=O>[CH2:20]([C:5]1[CH:4]=[CH:3][C:2]([O:29][C:25]2[CH:26]=[CH:27][CH:28]=[C:23]([F:22])[CH:24]=2)=[CH:7][C:6]=1[CH:8]1[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[O:11][C:10]([CH3:18])([CH3:17])[C:9]1=[O:19])[CH3:21]

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 4-(5-bromo-2-ethylphenyl)-2,2,6,6-tetramethylpyran-3,5-dione (200 mg, 0.57 mmol), 3-fluorophenol (320 mg, 2.83 mmol), cesium carbonate (400 mg, 1.13 mmol), copper(II) trifluoromethanesulfonate (10 mg, 0.03 mmol), and powdered 3 Å molecular sieves (400 mg) in toluene (3.5 ml) is heated to 160° C. under microwave irradiation for 60 minutes. The mixture is cooled to room temperature, poured into 2M aqueous hydrochloric acid, diluted with dichloromethane and filtered through a phase separation cartridge. The organic phase is collected. The solvent is evaporated under reduced pressure and the residue is purified by column chromatography on silica gel to give 4-[2-ethyl-5-(3-fluorophenoxy)phenyl]-2,2,6,6-tetramethylpyran-3,5-dione.

Workup

temperatureThe mixture is cooled to room temperature
filtrationfiltered through a phase separation cartridge
customThe organic phase is collected
customThe solvent is evaporated under reduced pressure
customthe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-85875c5401d242439bcad40ed895ea7a
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865623B2

Reaction notes

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