Potassium Carbonate → HCID 23004900, compound

HRID 1619650Notes

Reaction equation

HRID 1619650 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8](Br)[CH:7]=[CH:6][C:5]=1[OH:11])=[O:3].[F:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:11][C:5]1[CH:6]=[CH:7][C:8]([C:17]2[CH:18]=[CH:19][C:14]([C:13]([F:24])([F:23])[F:12])=[CH:15][CH:16]=2)=[CH:9][C:4]=1[C:2](=[O:3])[CH3:1]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 959915'-Bromo-2'-hydroxyacetophenoneHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 23004900HCID 23004900, compoundYield 162.7%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-bromo-2-hydroxy acetophenone (1.00 g, 4.65 mmol), 4-(trifluoromethyl)phenylboronic acid (1.32 g, 6.97 mmol), potassium carbonate (1.30 g, 9.38 mmol), tetrakis(triphenylphosphine)palladium (0) (538 mg, 0.465 mmol) in 1,4-dioxane (30.0 mL) and water (18.0 mL) was heated to 60° C. for 18 hours under nitrogen. The reaction was allowed to cool to room temperature and concentrated in vacuo to afford a dark brown oil which was dissolved in ethyl acetate (50 mL) and filtered through Arbocel™. The Arbocel™ was washed with ethyl acetate (100 mL). The combined organics were washed sequentially with a 0.5M aqueous solution of hydrogen chloride (2×50 mL) and brine (2×100 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford a brown oil (2.12 g). The oil was then purified by silica gel column chromatography (5%-10% ethyl acetate in heptane gradient elution) to afford the title compound as a yellow solid (795 mg, 61%).

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated in vacuo
  3. customto afford a dark brown oil which
  4. filtrationfiltered through Arbocel™
  5. washThe Arbocel™ was washed with ethyl acetate (100 mL)
  6. washThe combined organics were washed sequentially with a 0.5M aqueous solution of hydrogen chloride (2×50 mL) and brine (2×100 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-10abed5f594e42748db64bbee2b8aaab
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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