Phenylboronic Acid → HCID 58442404, compound

HRID 1465602Notes

Reaction equation

HRID 1465602 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 diatomaceous earth, 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, 1H), 7.25 (s, 2 H), 2.52 (s, 3H), 2.33 (s, 6 H).

Workup

  1. filtrationThe reaction mixture was filtered through a small pad of diatomaceous earth
  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-e182636a5d5e4fe6bb9eb309abb5e09f
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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