Hydrochloric Acid → HCID 22934542, compound

HRID 1354425Notes

Reaction equation

HRID 1354425 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[CH:4][CH:3]=1.C([Li])CCC.I[C:19]1[CH:29]=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=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>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]([C:19]3[CH:29]=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=3)=[CH:11][CH:12]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 142891Ethyl 4-iodobenzoateHCID 119716552-(4-chlorophenyl)thiopheneHCID 178418339Butyllithium

Product 1

HCID 22934542HCID 22934542, compoundYield 45%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution (15 ml) of 2-(4-chlorophenyl)thiophene (2.63 g) in tetrahydrofuran was added dropwise n-butyl lithium (1.6 M solution in hexane, 9.00 ml) under an argon atmosphere at −78° C. This mixed solution was heated to room temperature, and a solution (30 ml) of zinc chloride (2.04 g) in tetrahydrofuran was added. This mixture was stirred for 1 hr., and ethyl 4-iodobenzoate (1.16 ml) and tetrakis(triphenylphosphine)palladium (0.202 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. Ethanol (200 ml) was added to the residue, and the mixture was heated under reflux for 10 min. Insoluble materials were filtered off, and the filtrate was concentrated to give ethyl 4-[5-(4-chlorophenyl)-2-thienyl]benzoate (2.42 g, yield 45%) as a pale-green crystalline powder. melting point: 167–168° 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. additionEthanol (200 ml) was added to the residue
  7. temperaturethe mixture was heated
  8. temperatureunder reflux for 10 min
  9. filtrationInsoluble materials were filtered off
  10. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-945e09de0acd49e8860a306b6584aeee
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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