Phenylboronic Acid → HCID 58442404, compound

HRID 1843738Notes

Reaction equation

HRID 1843738 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14](=[O:16])[CH3:15])=[C:9]([CH3:17])[CH:8]=1)(=O)=O.[F-].[K+].[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>[CH3:17][C:9]1[CH:8]=[C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:12]=[C:11]([CH3:13])[C:10]=1[C:14](=[O:16])[CH3:15]

Participants

7

Reactant 3

HCID 66827Phenylboronic AcidHCID 522689Potassium FluorideHCID 20634999HCID 20634999, compound

Product 1

HCID 58442404HCID 58442404, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 75806TricyclohexylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-acetyl-3,5-dimethylphenyl trifluoromethanesulfonate (1.00 g, 3.38 mmol), KF (0.65 g, 11 mmol), and phenylboronic acid (0.49 g, 4.0 mmol) in THF (4.0 mL) was added tricyclohexylphosphine (11.4 mg, 0.04 mmol) and Pd(OAc)2 (7.6 mg, 0.03 mmol). The reaction mixture was stirred at room temperature for 5.0 h under N2. The reaction mixture was filtered through a small pad of Celite, and the cake was washed with ethyl acetate (40 mL). The filtrate was concentrated under reduced pressure, and the residue was purified by flash chromatography on silica gel to give 1-(3,5-dimethyl-[1,1′-biphenyl]-4-yl)ethanone (0.68 g) in 90% yield: 1H NMR (500 MHz, CDCl3) δ 7.56 (d, J=8.0 Hz, 2 H), 7.44 (t, J=7.0 Hz, 2 H), 7.35 (m, 1 H), 7.25 (s, 2 H), 2.52 (s, 3 H), 2.33 (s, 6 H).

Workup

  1. filtrationThe reaction mixture was filtered through a small pad of Celite
  2. washthe cake was washed with ethyl acetate (40 mL)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-4c9eb1e7f8c7424298b98d4c7122db14
Source dataset
uspto-grants-2015_02
Patent number
US08946268B2

Reaction notes

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