P-Chloroacetophenone → 4-Acetylbiphenyl

HRID 1014776Notes

Reaction equation

HRID 1014776 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7](Cl)=[CH:6][CH:5]=1)=[O:3].[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[F-].[Cs+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2C=CC=CC=2)C2[C-](N(C)C)C=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2]>[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][CH:5]=1)=[O:3]

Participants

7

Reactant 3

HCID 7467P-ChloroacetophenoneHCID 25953Cesium fluorideHCID 66827Phenylboronic Acid

Product 1

HCID 71134-AcetylbiphenylYield 88%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1317290462-Diphenylphosphino-dimethylaminoferroceneCatalystHCID 312751,4-DioxaneSolvent

Procedure

According to General Procedure A, a mixture of 4-chloroacetophenone (65 μL, 0.50 mmol), phenylboronic acid (91 mg, 0.75 mmol), CsF (228 mg, 1.50 mmol), Pd(OAc)2 (2 mg, 0.01 mmol) and ligand 12f (8 mg, 0.02 mmol) in 1,4-dioxane (2.5 mL) was heated to reflux, cooled and filtered. After evaporation of the solvent, recrystallization from hexane containing a small amount of EtOAc gave 51b (86 mg, 88%) as colorless crystals. 1H NMR (300 MHz, CDCl3) δ 8.05 (d, 2H, J=8.4 Hz), 7.69 (d, 2H, J=8.4 Hz), 7.63 (d, 2H, J=7.2 Hz), 7.50-7.40 (m, 3H), 2.64 (s, 3H); 13C NMR (75.5 MHz, CDCl3) δ 197.7, 145.8, 139.8, 135.8, 128.93, 128.89, 128.2, 127.24, 127.20, 26.6.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperaturecooled
  4. filtrationfiltered
  5. customAfter evaporation of the solvent, recrystallization from hexane containing a small amount of EtOAc

Sources & evidence

ORD record
ord-b669fc9253d449eb83896d3b0f17e653
Source dataset
uspto-grants-2011_07
Patent number
US07982064B2

Reaction notes

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