Hydrochloric Acid → HCID 22934551, compound

HRID 1354407Notes

Reaction equation

HRID 1354407 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[CH:3]1.C([Li])(C)(C)C.Br[C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=1.Cl>O1CCCC1.[Cl-].[Zn+2].[Cl-].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 73041-MethylpyrroleHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 178418306HCID 178418306, compound

Product 1

HCID 22934551HCID 22934551, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution (50 ml) of 1-methylpyrrole (4.44 ml) in tetrahydrofuran was added dropwise t-butyl lithium (1.7 M solution in pentane, 30.0 ml) under an argon atmosphere at −78° C. This mixed solution was heated to room temperature, and a solution (100 ml) of zinc chloride (75.0 g) in tetrahydrofuran was added. This mixture was stirred for 1 hr., and 1-bromo-4-trifluoromethylbenzene (3.50 ml) and tetrakis(triphenylphosphine)palladium (0.722 g) were added. This mixture was stirred overnight under an argon atmosphere, and 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=5:1, volume ratio) to give 1-methyl-2-(4-trifluoromethylphenyl)pyrrole (4.01 g, yield 71%) as a colorless crystalline powder. melting point: 39–40° C.

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=5:1, volume ratio)

Sources & evidence

ORD record
ord-980d2dfb981c42fead90a82726364887
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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