Ethyl Acetate → 5'-Isopropyl-5,2'-dimethoxy-2-nitro-4-trifluoromethyl-biphenyl

HRID 604175Notes

Reaction equation

HRID 604175 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:20]([F:23])([F:22])[F:21])=[CH:5][C:6]([N+:17]([O-:19])=[O:18])=[C:7](OS(C(F)(F)F)(=O)=O)[CH:8]=1.[CH:24]([C:27]1[CH:28]=[CH:29][C:30]([O:36][CH3:37])=[C:31](B(O)O)[CH:32]=1)([CH3:26])[CH3:25].C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>O1CCOCC1>[CH:24]([C:27]1[CH:28]=[CH:29][C:30]([O:36][CH3:37])=[C:31]([C:7]2[CH:8]=[C:3]([O:2][CH3:1])[C:4]([C:20]([F:23])([F:22])[F:21])=[CH:5][C:6]=2[N+:17]([O-:19])=[O:18])[CH:32]=1)([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 45891905-Isopropyl-2-methoxyphenylboronic acidHCID 86626908Trifluoromethanesulfonic acid 5-methoxy-2-nitro-4-trifluoromethyl-phenyl ester

Product 1

HCID 666031075'-Isopropyl-5,2'-dimethoxy-2-nitro-4-trifluoromethyl-biphenylYield 90.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Trifluoromethanesulfonic acid 5-methoxy-2-nitro-4-trifluoromethyl-phenyl ester (2.6 g) is dissolved in 1,4-dioxane (20 ml) and thereto is added 5-isopropyl-2-methoxybenzene boronic acid (1.5 g), [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium dichloromethane complex (575 mg) and cesium carbonate (3.44 g), and the mixture is stirred under nitrogen atmosphere at 80° C. overnight. The reaction solution is cooled to room temperature, and thereto are added ethyl acetate and a saturated aqueous sodium bicarbonate solution, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=49:1→17:3) to give 5′-isopropyl-5,2′-dimethoxy-2-nitro-4-trifluoromethyl-biphenyl (2.35 g). MS (m/z): 370 [M+H]+

Workup

  1. temperatureThe reaction solution is cooled to room temperature
  2. customa saturated aqueous sodium bicarbonate solution, and the mixture is separated
  3. washthe organic layer is washed with a saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=49:1→17:3)

Sources & evidence

ORD record
ord-722ae2a1e47b4ea29d2e9e66b0a3dcf3
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

Loading…