Hydrochloric Acid → HCID 10910588, compound

HRID 1877235Notes

Reaction equation

HRID 1877235 reaction equation
Br[C:2]1[S:6][C:5]([CH3:7])=[C:4]([CH:8]2[O:12]CCO2)[CH:3]=1.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[NH4+].Cl>O1CCCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl.CN(C)C=O.O>[CH3:7][C:5]1[S:6][C:2]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:3][C:4]=1[CH:8]=[O:12]

Participants

11

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 66827Phenylboronic AcidHCID 68516498HCID 68516498, compound

Product 1

HCID 10910588HCID 10910588, compoundYield 61%

Reagents, catalysts & solvents 5

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 2-(5-bromo-2-methylthiophen-3-yl)-1,3-dioxolane (3.50 g) synthesized above, phenylboronic acid (2.56 g), sodium carbonate (2.96 g), water (10 mL) and N,N-dimethylformamide (50 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II).dichloromethane adduct (1.14 g). The reaction mixture was deaerated, and the mixture was stirred at 80° C. for 3 hr under an argon atmosphere. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated sodium hydrogen carbonate and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20% ethyl acetate/hexane) to give a yellow oil. To a solution of the obtained oil in tetrahydrofuran (20 mL) was added 1N hydrochloric acid (10 mL), and the mixture was stirred at room temperature for 1 hr. Tetrahydrofuran was evaporated using evaporator, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure to give the title compound (1.72 g, 61%) as a pale-yellow solid.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated sodium hydrogen carbonate and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (20% ethyl acetate/hexane)
  8. customto give a yellow oil
  9. stirringthe mixture was stirred at room temperature for 1 hr
  10. customTetrahydrofuran was evaporated
  11. customevaporator
  12. extractionthe mixture was extracted with ethyl acetate
  13. washThe extract was washed with saturated brine
  14. dry with materialdried over magnesium sulfate
  15. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-473568a6529141918211864c1556a27e
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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