Sulfuric Acid → 3-(4-(Methylthio)phenyl)-2-phenylinden-1-one

HRID 2269571Notes

Reaction equation

HRID 2269571 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][CH:3]=1.C([Li])CCC.CCCCCC.[CH:21](=[C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:30](=[O:31])O1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.OS(O)(=O)=O.C([O-])(O)=O.[Na+]>C1COCC1.C1C=CC=CC=1.CCOC(C)=O.O>[CH3:9][S:8][C:5]1[CH:6]=[CH:7][C:2]([C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:30](=[O:31])[C:21]=2[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:3][CH:4]=1

Participants

11

Reactant 6

HCID 1118Sulfuric AcidHCID 8058HexaneHCID 660374-BromothioanisoleHCID 68464BenzylidenephthalideHCID 516892Sodium BicarbonateHCID 178418339Butyllithium

Product 1

HCID 153373993-(4-(Methylthio)phenyl)-2-phenylinden-1-one

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of p-bromothioanisole (2.04 g, 10 mmol) in THF (40 mL) cooled to −78° C. was added a solution of n-butyl lithium in hexane (4.0 mL of 2.5 M, 10 mmol). The resulting suspension was stirred at this temperature for 20 min. Then a solution of benzalphthalide (2.11 g, 9.5 mmol) in benzene (20 mL) was added and the reaction was allowed to proceed at r.t. for 2 hrs. The reaction turned deep-red. The reaction was completed by addition of conc. H2SO4 (0.63 mL, 20 mmol) and stirred at r.t. for another 30 min. The reaction was then diluted with EtOAc and a 1:1 mixture of H2O and saturated aqueous NaHCO3 and extracted. The aqueous layer was extracted one more time with EtOAc. The combined organic extracts were dried over MgSO4 and concentrated to dryness. The crude product was purified by flash chromatography eluted with 10-15% EtOAc in hexane to give the title compound as an orange-red gum.

Workup

  1. waitto proceed at r.t. for 2 hrs
  2. stirringstirred at r.t. for another 30 min
  3. extractionextracted
  4. extractionThe aqueous layer was extracted one more time with EtOAc
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. concentrationconcentrated to dryness
  7. customThe crude product was purified by flash chromatography
  8. washeluted with 10-15% EtOAc in hexane

Sources & evidence

ORD record
ord-c1117e95d8b44abca1783fa5d7ec6e04
Source dataset
uspto-grants-2001_12
Patent number
US06329421B1

Reaction notes

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