Hydrochloric Acid → HCID 54240790, compound

HRID 1599509Notes

Reaction equation

HRID 1599509 reaction equation
Br[C:2]1[CH:6]=[CH:5][S:4][CH:3]=1.Cl.[C:8](=[O:11])(O)[O-].[Na+]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.O1CCCC1>[CH:8]([C:3]1[S:4][C:5]([C:3]2[S:4][C:5]([C:2]3[CH:6]=[CH:5][S:4][CH:3]=3)=[CH:6][CH:2]=2)=[CH:6][CH:2]=1)=[O:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 133833-BromothiopheneHCID 516892Sodium Bicarbonate

Product 1

HCID 54240790HCID 54240790, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a two-necked round bottomed flask was added 5-dimethoxymethyl-5'-tributyl-stannyl-2,2'-bithiophene (5.6 g), bis(triphenylphosphine)palladium (II) chloride (0.32 g), 3-bromo-thiophene (1.5 g) (Aldrich Chem. Co., Milwaukee, Wis.) and tetrahydrofuran (20 ml). The reaction mixture was refluxed for 16 hours. To the reaction mixture was then added hydrochloric acid (1N, 3 ml) and was further refluxed for 3 hours. Saturated sodium bicarbonate aqueous solution was added to neutrality and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was separated by silica gel chromatography, eluted with n-hexane/ethyl acetate (9:1 →1:1 gradient) to give brownish solid product (0.7 g, 40%), melting point 155°-157° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was separated by silica gel chromatography
  7. washeluted with n-hexane/ethyl acetate (9:1 →1:1 gradient)

Sources & evidence

ORD record
ord-bc4f074177434e2fa06689f0ae5806e3
Source dataset
uspto-grants-1998_04
Patent number
US05741811

Reaction notes

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