Chlorotrimethylsilane → HCID 22125122, compound

HRID 1858335Notes

Reaction equation

HRID 1858335 reaction equation
BrCCBr.Cl[Si](C)(C)C.I[CH2:11][CH2:12][CH2:13][N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24].I[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-:34])=[O:33])[CH:27]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CN(C)C=O.[Zn].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N+:32]([C:28]1[CH:27]=[C:26]([CH2:11][CH2:12][CH2:13][N:14]2[C:18](=[O:19])[C:17]3[C:16](=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:15]2=[O:24])[CH:31]=[CH:30][CH:29]=1)([O-:34])=[O:33]

Participants

9

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 78391,2-DibromoethaneHCID 125741-Iodo-3-nitrobenzeneHCID 80271Tri-o-tolylphosphineHCID 2302832-(3-Iodo-propyl)-isoindole-1,3-dione

Product 1

HCID 22125122HCID 22125122, compoundYield 20.4%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Under an atmosphere of nitrogen, a stirred suspension of 1.6 g (24 mg.atom) of zinc dust (<10 micron diameter) in 20 ml of dimethylformamide was treated with 0.11 ml (1.2 mmol) of 1,2-dibromoethane and the mixture was heated to 60° C. then allowed to cool to room temperature. The heating and cooling was repeated twice more. 0.04 ml (0.24 mmol) of chlorotrimethylsilane was added and the mixture stirred at ambient temperature for 30 minutes. The mixture was then treated with 1.26 g (4 mmol) of N-(3-iodopropyl)phthalimide and the resulting suspension stirred for 30 minutes at ambient temperature and then heated at 35° C. for 1 hour and cooled. To the mixture were then added sequentially 750 mg (3 mmol) of 1-iodo-3-nitrobenzene, 60 mg (0.06 mmol) of tris(dibenzylideneacetone)dipalladium and 70 mg (0.23 mmol) of tri(o-tolyl)phosphine and the resulting mixture stirred at ambient temperature for 1 hour. The suspension was filtered and the filtrate diluted with 50 ml of ethyl acetate, washed twice with 40 ml of water, dried over magnesium sulfate, filtered and evaporated. The product was purified by flash chromatography on silica gel using ethyl acetate/isohexane in a ratio of 1:2 as eluent. Product containing fractions were combined and evaporated to give 190 mg (20%) of 2-[3-(3-nitrophenyl)-propyl]-isoindole-1,3-dione as a pale pink solid. [Mass spectrum (ESI) MH+ =311].

Workup

  1. temperatureto cool to room temperature
  2. temperatureThe heating and cooling
  3. stirringthe resulting suspension stirred for 30 minutes at ambient temperature
  4. temperatureheated at 35° C. for 1 hour
  5. temperaturecooled
  6. stirringthe resulting mixture stirred at ambient temperature for 1 hour
  7. filtrationThe suspension was filtered
  8. additionthe filtrate diluted with 50 ml of ethyl acetate
  9. washwashed twice with 40 ml of water
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. customevaporated
  13. customThe product was purified by flash chromatography on silica gel
  14. additionProduct containing fractions
  15. customevaporated

Sources & evidence

ORD record
ord-11d2a235c67e468ead4abd48836145b1
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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