Cesium carbonate → 2-(2,4-Dichloro-phenyl)-1-(4-trifluoromethyl-phenyl)ethanone

HRID 526683Notes

Reaction equation

HRID 526683 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1I.C([O-])([O-])=O.[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[F:58][C:59]([F:70])([F:69])[C:60]1[CH:65]=[CH:64][C:63]([C:66](=[O:68])[CH3:67])=[CH:62][CH:61]=1>O1CCOCC1.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]>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:67][C:66]([C:63]1[CH:64]=[CH:65][C:60]([C:59]([F:58])([F:69])[F:70])=[CH:61][CH:62]=1)=[O:68]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 697311-(4-(Trifluoromethyl)phenyl)ethan-1-oneHCID 968642,4-Dichloro-1-iodobenzeneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

Product 1

HCID 634119132-(2,4-Dichloro-phenyl)-1-(4-trifluoromethyl-phenyl)ethanone

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 6 g of 2,4-Dichloro-1-iodo-benzene, 15.7 g of Cs2CO3, 63 mg of Pd(dba)2 (Bis(dibenzylidenacetonpalladium), 127 mg of Xantphos (9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene) and 8.3 g of 1-(4-Trifluoromethyl-phenyl)ethanone in 45 ml of dioxane was heated under argon for 30 min at 150° C. by microwave irradiation. After cooling to room temperature and dilution with saturated aqueous sodium hydrogen carbonate solution, the reaction mixture was filtered through a chem Elut® cartridge by eluting with ethyl acetate. The solvents were removed under reduced pressure and the crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate. The fractions containing the product were combined and the solvent evaporated under reduced pressure. Yield: 9.1 g.

Workup

  1. filtrationdilution with saturated aqueous sodium hydrogen carbonate solution, the reaction mixture was filtered through a chem Elut® cartridge
  2. washby eluting with ethyl acetate
  3. customThe solvents were removed under reduced pressure
  4. customthe crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate
  5. additionThe fractions containing the product
  6. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-25976006cf774118a5787344bad906f5
Source dataset
uspto-grants-2016_05
Patent number
US09346757B2

Reaction notes

Loading…