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

HRID 1669224Notes

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]

Participants

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

customthe reaction mixture is degassed with nitrogen for 20 min
customconsumption of starting material
concentrationThe reaction mixture is concentrated
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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