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Potassium Carbonate → 1-(3-Methyl-4'-trifluoromethyl-biphenyl-4-yl)-ethanone

HRID 1669224
Notes
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Reaction equation

HRID 1669224 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7](OS(C(F)(F)F)(=O)=O)=[CH:6][C:5]=1[CH3:18])(=[O:3])[CH3:2].[F:19][C:20]([F:31])([F:30])[C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O.CCCCCC>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:18][C:5]1[CH:6]=[C:7]([C:24]2[CH:25]=[CH:26][C:21]([C:20]([F:31])([F:30])[F:19])=[CH:22][CH:23]=2)[CH:8]=[CH:9][C:4]=1[C:1](=[O:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 114829354-Acetyl-3-methylphenyl trifluoromethanesulfonateHCID 21226206Ethyl acetate hexane

Product 1

HCID 673427591-(3-Methyl-4'-trifluoromethyl-biphenyl-4-yl)-ethanoneYield 96%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

To an ambient temperature solution of trifluoro-methanesulfonic acid 4-acetyl-3-methyl-phenyl ester (6.10 g, 21.61 mmol) in dioxane/water (150/30 mL) is added 4-(trifluoromethyl)phenylboronic acid (4.51 g, 23.77 mmol), potassium carbonate (4.48 g, 32.42 mmol) and the reaction mixture is degassed with nitrogen for 20 min. Tetrakis(triphenylphosphine)palladium (1.25 g, 1.08 mmol) is added and the reaction mixture is heated to 80° C. overnight. TLC (10% EtOAc/hexane) indicates complete consumption of starting material. The reaction mixture is concentrated and chromatographed (330 g SiO2, 5% EtOAc/Hexanes) to yield the title compound (5.77 g, 96%). 1NMR (400 MHz, CDCl3) δ ppm: 7.82 (d, 1H, J=7.9 Hz), 7.72 (s, 4H), 7.51-7.46 (m, 2H), 2.63 (s, 3H), 2.62 (s, 3H).

Workup

  1. customthe reaction mixture is degassed with nitrogen for 20 min
  2. customconsumption of starting material
  3. concentrationThe reaction mixture is concentrated
  4. customchromatographed (330 g SiO2, 5% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-054080ad3a9c4cc4aee96800ee2270fb
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07989457B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes