Ethyl Acetate → HCID 1393772, compound

HRID 1929395Notes

Reaction equation

HRID 1929395 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)=[O:4].[Br:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17](I)[CH:16]=1.[F-].[Cs+].C(OCC)(=O)C>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Br:14][C:15]1[CH:16]=[C:17]([C:8]2[CH:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=2)[CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11561Benzene, 1-bromo-3-iodo-HCID 25953Cesium fluorideHCID 27343694-Methoxycarbonylphenylboronic acid

Product 1

HCID 1393772HCID 1393772, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

4-(Methoxycarbonyl)phenylboronic acid (1.55 g, 8.63 mmol), 1-bromo-3-iodobenzene (2.22 g, 7.84 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.29 g, 0.392 mmol), and CsF (2.38 g, 15.7 mmol) in dioxane (40 mL) were stirred at 80° C. for 8 hours. The reaction was cooled, poured into ethyl acetate, washed twice with water and brine, and the combined organic layers were concentrated. The residue was chromatographed on silica gel using 2-20% ethyl acetate in hexanes afford the title compound.

Workup

  1. temperatureThe reaction was cooled
  2. washwashed twice with water and brine
  3. concentrationthe combined organic layers were concentrated
  4. customThe residue was chromatographed on silica gel using 2-20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-4731290debc84ad883f42ea2d7df7e9b
Source dataset
uspto-grants-2012_05
Patent number
US08188077B2

Reaction notes

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