Hydrochloric Acid → HCID 22934574, compound

HRID 1354418Notes

Reaction equation

HRID 1354418 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)=[CH:5][CH:4]=1.C([Li])CCC.Br[C:22]1[CH:32]=[CH:31][CH:30]=[CH:29][C:23]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25].Cl>O1CCCC1.[Cl-].[Zn+2].[Cl-]>[F:15][C:2]([F:1])([F:14])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:10][C:11]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:22][C:23]=3[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:12][CH:13]=2)=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 80186Ethyl 2-bromobenzoateHCID 106561512-(4-Trifluoromethylphenyl)furanHCID 178418339Butyllithium

Product 1

HCID 22934574HCID 22934574, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution (25 ml) of 2-(4-trifluoromethylphenyl)furan (3.18 g) in tetrahydrofuran was added dropwise n-butyl lithium (1.6 M solution in hexane, 10.0 ml) under an argon atmosphere at −78° C. This mixed solution was heated to room temperature, and a solution (30 ml) of zinc chloride (2.25 g) in tetrahydrofuran was added. This mixture was stirred for 1 hr., and then ethyl 2-bromobenzoate (2.38 ml) and tetrakis (triphenylphosphine)palladium (0.433 g) were added. This mixture was stirred overnight under an argon atmosphere, and then poured into 0.5 M hydrochloric acid. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1, volume ratio) to give ethyl 2-[5-(4-trifluoromethylphenyl)-2-furyl]benzoate (2.54 g, yield 47%) as a pale-yellow oil. NMR (CDCl3) δ: 1.12 (3H, t, J=7.2 Hz), 4.27 (2H, q, J=7.2 Hz), 6.70 (1H, d, J=3.6 Hz), 6.87 (1H, d, J=3.6 Hz), 7.41 (1H, dt, J=1.4, 7.4 Hz), 7.53 (1H, dt, J=1.4, 7.4 Hz), 7.61–7.79 (6H, m).

Workup

  1. stirringThis mixture was stirred overnight under an argon atmosphere
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1, volume ratio)

Sources & evidence

ORD record
ord-2b93c067bf0c4785852495082ede184b
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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