Hydrochloric Acid → Bis(2-methyl-3-phenyl-1H-inden-7-yl) sulfide

HRID 2357868Notes

Reaction equation

HRID 2357868 reaction equation
[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[S:11][C:12]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:13]=2[CH2:14][CH:15]([CH3:22])[C:16]3=O)[C:3]1=O.[C:24]1([Mg]Br)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[Mg].Br[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.Cl>CCOCC.O>[CH3:1][C:2]1[CH2:10][C:9]2[C:4]([C:3]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[CH:5][CH:6]=[CH:7][C:8]=2[S:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:13]=1[CH2:14][C:15]([CH3:22])=[C:16]2[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7961BromobenzeneHCID 5462224MagnesiumHCID 588977942-methyl-4-[(2-methyl-1-oxo-2,3-dihydro-1H-inden-4-yl)sulfanyl]-1-indanoneHCID 178418255HCID 178418255, compound

Product 1

HCID 58897800Bis(2-methyl-3-phenyl-1H-inden-7-yl) sulfide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

Under an argon atmosphere, to a solution of 3.20 g (9.93 mmol) of 2-methyl-4-[(2-methyl-1-oxo-2,3-dihydro-1H-inden-4-yl)sulfanyl]-1-indanone in 20 ml of ether, a solution of PhMgBr in ether [obtained from 0.73 g (30.0 mmol) of magnesium turnings, 4.77 g (30.4 mmol) of bromobenzene, and 30 ml of ether] was added dropwise with vigorous stirring at 0° C. This mixture was stirred overnight and then added to 50 ml of water. Then, to this mixture 12 M HCl (to pH 1) was added. The organic layer was separated; and the aqueous layer was extracted with 3×20 ml of dichloromethane. The combined extract was evaporated, and a mixture of the residue and 0.5 g para-toluenesulfonic acid in 150 ml benzene was refluxed for 1 hour. The resulting mixture was washed with 50 ml of saturated aqueous NaHCO3. The organic layer was separated, dried over Na2SO4, and evaporated to dryness. The product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 35 mm, l 300 mm, eluant: hexanes-CH2Cl2=1:2, vol.). Yield, 2.20 g (50%) of a yellowish solid.

Workup

  1. stirringThis mixture was stirred overnight
  2. customThe organic layer was separated
  3. extractionand the aqueous layer was extracted with 3×20 ml of dichloromethane
  4. extractionThe combined extract
  5. customwas evaporated
  6. additiona mixture of the residue and 0.5 g para-toluenesulfonic acid in 150 ml benzene
  7. temperaturewas refluxed for 1 hour
  8. washThe resulting mixture was washed with 50 ml of saturated aqueous NaHCO3
  9. customThe organic layer was separated
  10. dry with materialdried over Na2SO4
  11. customevaporated to dryness
  12. customThe product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 35 mm, l 300 mm, eluant: hexanes-CH2Cl2=1:2, vol.)
  13. customYield

Sources & evidence

ORD record
ord-d44296ed4d704db3a0c32e34abadeead
Source dataset
uspto-grants-2010_07
Patent number
US07763562B2

Reaction notes

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