Toluene → 1-(4'-Methyl[1,1'-biphenyl]-2-yl)ethanone

HRID 1387703Notes

Reaction equation

HRID 1387703 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.[F-].[Cs+].Cl[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20](=[O:22])[CH3:21].C1(C)C=CC=CC=1>CCOCC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[C:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)(=[O:22])[CH3:21]

Participants

7

Reactant 4

HCID 1140TolueneHCID 25953Cesium fluorideHCID 72864Ethanone, 1-(2-chlorophenyl)-HCID 79799Tolylboronic acid

Product 1

HCID 98372111-(4'-Methyl[1,1'-biphenyl]-2-yl)ethanoneYield 94.2%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
110 °C

Procedure

A solid mixture of 4-methylphenylboronic acid (204 mg, 1.5 mmol), CsF (456 mg, 3.0 mmol), Pd(dba)2 (3 mg, 5 μmol), and ligand 1 (5 mg, 15 μmol) was thoroughly evacuated and purged with argon. 2′-Chloroacetophenone (0.13 mL, 1.0 mmol) and toluene (4 mL) were added and the reaction was heated at 110° C. for 1 h. GC-MS analysis indicated the reaction to be complete, i.e. starting aryl chloride reagent was completely consumed (quantitative GC yield). The reaction was taken up in ether (100 mL) and washed with H2O (30 mL) and brine (30 mL), The organic phase was dried over MgSO4, filtered and concentrated under vacuum. The crude product was purified by column chromatography on silica gel using hexanes:ethyl acetate (8:1) as eluant to afford the title compound as a yellow oil (198 mg, 92% isolated yield) after drying under vacuum. TON≈100 and TOF≈100. 1 H NMR (CDCl3): δ7.52 (d, J=8.4, 1H, ArH), 7.47 (d, J=7.2, 1H, ArH), 7.38 (t, J=7.2, 2H, ArH), 7.22 (s, 4H, ArH), 2.39 (s, 3H, C(O)CH3), 2.00 (s, 3H, ArCH3). 13C{1H} NMR (CDCl3): δ205.1, 140.9, 140.5, 137.8, 137.7, 130.6, 130.2, 129.4, 128.7, 127.8, 127.2, 30.4, 21.2.

Workup

  1. customwas thoroughly evacuated
  2. custompurged with argon
  3. customthe reaction
  4. customwas completely consumed
  5. custom(quantitative GC yield)
  6. washwashed with H2O (30 mL) and brine (30 mL)
  7. dry with materialThe organic phase was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ea77db3c45d040839b2551c9585664e6
Source dataset
uspto-grants-2001_07
Patent number
US06268513B1

Reaction notes

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