Sodium Carbonate → 1-(2′-Chloro[1,1′-biphenyl]-3-yl)ethanone

HRID 1394166Notes

Reaction equation

HRID 1394166 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[Cl:8].[C:9]([C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1)(=[O:11])[CH3:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)CC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Cl:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:16]1[CH:15]=[CH:14][CH:13]=[C:12]([C:9](=[O:11])[CH3:10])[CH:17]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 119931-Chloro-2-iodobenzeneHCID 27343103-Acetylphenylboronic acid

Product 1

HCID 51285771-(2′-Chloro[1,1′-biphenyl]-3-yl)ethanone

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 10311-PropanolSolvent

Procedure

To a solution of iodochlorobenzene (8.64 g, 55 mmol) in n-propanol (85.8 mL), 3-acetylphenylboronic acid (10.0 g, 50 mmol) was added and the solution was stirred for 2 min. Then triphenylphosphine (118 mg, 0.45 mmol), palladium acetate (33 mg, 0.15 mmol), 2M sodium carbonate (30 mL, 60 mmol) and water (17.68 mL) were added and the reaction mixture was refluxed for 16 h. It was quenched with water and partitioned between ethyl acetate and water, washed with saturated sodium bicarbonate, brine and dried over sodium sulfate. Finally it was filtered, concentrated and purified by chromatography (hexane:ethyl acetate; 4:1) to yield the product.

Workup

  1. temperaturethe reaction mixture was refluxed for 16 h
  2. customIt was quenched with water
  3. custompartitioned between ethyl acetate and water
  4. washwashed with saturated sodium bicarbonate, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationFinally it was filtered
  7. concentrationconcentrated
  8. custompurified by chromatography (hexane:ethyl acetate; 4:1)
  9. customto yield the product

Sources & evidence

ORD record
ord-860d34109b44441fa1734be314113d61
Source dataset
uspto-grants-2008_03
Patent number
US07348348B2

Reaction notes

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