Water → 3-Methoxy-1-(5-phenyl-2-thienyl)naphthalene

HRID 2369638Notes

Reaction equation

HRID 2369638 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]([O:17][CH3:18])[CH:8]=1)(=O)=O.[C:21]1([C:27]2[S:31][C:30](B(O)O)=[CH:29][CH:28]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C1(C)C=CC=CC=1.C(O)C.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>[CH3:18][O:17][C:9]1[CH:8]=[C:7]([C:30]2[S:31][C:27]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:28][CH:29]=2)[C:16]2[C:11]([CH:10]=1)=[CH:12][CH:13]=[CH:14][CH:15]=2

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2776315(5-Phenylthiophen-2-yl)boronic acidHCID 222228613-Methoxynaphthalen-1-yl Trifluoromethanesulfonate

Product 1

HCID 582741703-Methoxy-1-(5-phenyl-2-thienyl)naphthaleneYield 67%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of 3-methoxynaphthalene-1-yl trifluoromethanesulfonate (2.7 g, 8.82 mmol), 5-phenyl-2-thiopheneboronic acid (2.7 g, 13.24 mmol), sodium carbonate (1.4 g, 13.24 mmol) was mixed in de-gassed toluene (50 ml) and ethanol (50 ml), under nitrogen. Pd(PPh3)4 (153 mg, 1 mol %) was added and the mixture heated to reflux for 18 h. The solution was allowed to cool, poured into water (200 ml), extracted with dichloromethane (2×100 ml), dried (Na2SO4), and the solvent removed under reduced pressure. The resulting residue was dissolved in DCM and filtered through a short plug of silica. The solvent was removed under reduced pressure to give a red/brown solid, which was flash chromatographed on silica using EtOAc-hexane (1:9). The fractions were combined and the solvent removed to give the title compound (1.87 g, 67%) as a green solid.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 18 h
  3. temperatureto cool
  4. extractionextracted with dichloromethane (2×100 ml)
  5. dry with materialdried (Na2SO4)
  6. customthe solvent removed under reduced pressure
  7. dissolutionThe resulting residue was dissolved in DCM
  8. filtrationfiltered through a short plug of silica
  9. customThe solvent was removed under reduced pressure
  10. customto give a red/brown solid, which
  11. customchromatographed on silica
  12. customthe solvent removed

Sources & evidence

ORD record
ord-fbeceefa1c84424a9eebcc48769fc65c
Source dataset
uspto-grants-2014_04
Patent number
US08703978B2

Reaction notes

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