Potassium Carbonate → HCID 22283537, compound

HRID 1062908Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:15]=[C:14](F)[CH:13]=[CH:12][C:9]=1[CH:10]=[O:11].[CH2:17]([O:24][C:25]1[CH:26]=[C:27]([OH:31])[CH:28]=[CH:29][CH:30]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C>[CH2:17]([O:24][C:25]1[CH:26]=[C:27]([CH:28]=[CH:29][CH:30]=1)[O:31][C:14]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[C:8]([Cl:7])[CH:15]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Potassium carbonate (5.53 g) was added to a DMF solution (70 ml) of 2-chloro-4-fluorobenzaldehyde (3.35 g) and 3-benzyloxyphenol (4.23 g) and the solution was stirred for 3 hours while heated to 150° C. The reaction mixture was decanted into water and was extracted with ethyl acetate. The organic phase was sequentially washed with water and a saturated aqueous solution of sodium chloride and was dried with anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1). In this manner, the desired product (6.73 g) was obtained as a colorless powder.

Workup

customThe reaction mixture was decanted into water
extractionwas extracted with ethyl acetate
washThe organic phase was sequentially washed with water
dry with materiala saturated aqueous solution of sodium chloride and was dried with anhydrous sodium sulfate
customThe solvent was removed by distillation under reduced pressure
customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1)

Sources & evidence

ORD record: ord-80467e84bb7b4dfa9ca5e33f1b6dd64d
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06963012B2

Reaction notes

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