Dichloromethane → 1-(4'-Hydroxy-1,1'-biphenyl-3-yl)ethanone

HRID 494861Notes

Reaction equation

HRID 494861 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9]([C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1)(=[O:11])[CH3:10].C([O-])([O-])=O.[Na+].[Na+].C(Cl)Cl>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([C:9](=[O:11])[CH3:10])[CH:17]=2)=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 108944-IodophenolHCID 27343103-Acetylphenylboronic acid

Product 1

HCID 112181061-(4'-Hydroxy-1,1'-biphenyl-3-yl)ethanoneYield 95%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

4-Iodophenol (5.39 g, 24.5 mmol) and 3-acetylphenylboronic acid (4.42 g, 26.95 mmol) were mixed in N,N-dimethylformamide (15 mL) and treated with 1.0 M aqueous Na2CO3 (75 mL) and palladium (II) acetate (110 mg, 0.49 mmol). The suspension was heated at 55° C. for one hour and then brought to room temperature. CH2Cl2 (100 mL) was added to the mixture which was then filtered. The aqueous layer of the filtrate was extracted with CH2Cl2 and the combined organic phases were washed consecutively with pH 6 potassium phosphate buffer and brine, then dried (Na2SO4), concentrated, and chromatographed through silica with a 33 to 100% gradient of hexanes/CH2Cl2 followed by a gradient of 0 to 3% EtOAc/CH2Cl2. Impure fractions were combined, concentrated, and rechromatographed as before, twice, to provide the title compound as an oil which slowly crystallized to a white solid upon standing (˜95% yield). MS (ESI APCI negative ion detection) m/z 211 (M−H)−; 1HNMR (300 MHz, CDCl3) δ 2.65 (s, 3H), 6.97 (d, 2H), 7.47-7.53 (m, 3H), 7.74 (ddd, 1H), 7.88 (ddd, 1H), 8.13 (dd, 1H).

Workup

  1. custombrought to room temperature
  2. filtrationwas then filtered
  3. extractionThe aqueous layer of the filtrate was extracted with CH2Cl2
  4. washthe combined organic phases were washed consecutively with pH 6 potassium phosphate buffer and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customchromatographed through silica with a 33 to 100% gradient of hexanes/CH2Cl2
  8. concentrationconcentrated
  9. customrechromatographed as before, twice,

Sources & evidence

ORD record
ord-91069ddf929c496e9daf055487daa4a3
Source dataset
uspto-grants-2009_05
Patent number
US07538138B2

Reaction notes

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