Potassium Carbonate → Ethyl 2-((4-fluorophenyl)methyl)-3-oxo-3-(4-(trifluoromethyl)phenyl)propionate

HRID 1610472

Reaction equation

[O:1]=[C:2]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][CH:3]([C:2](=[O:1])[C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:11][CH:10]=2)[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of ethyl 3-oxo-3-(4-trifluoromethylphenyl)propionate (38.2 g, 0.147 mol), 4-fluorobenzyl bromide (25 g, 0.13 mol), potassium carbonate (36.6 g, 0.26 mol) and acetonitrile (500 ml) was stirred at 60° C. for 3 hrs. The reaction solution was concentrated under reduced pressure, and water (500 ml) was added. The mixture was extracted with ethyl acetate (500, 200 ml). The extract was washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1-10:1, hexane:toluene=1:1) and crystallized from cold hexane to give ethyl 2-((4-fluorophenyl)methyl)-3-oxo-3-(4-(trifluoromethyl)phenyl)propionate (29.5 g, 55%).

Workup

concentrationThe reaction solution was concentrated under reduced pressure, and water (500 ml)
additionwas added
extractionThe mixture was extracted with ethyl acetate (500, 200 ml)
washThe extract was washed with water
dry with materialdried over anhydrous magnesium sulfate
customevaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1-10:1, hexane:toluene=1:1)
customcrystallized from cold hexane

Sources & evidence

ORD record: ord-1122205c20d345ca8b325883035c9457
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06982348B2

Linked notes

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