Dimethyl Sulfoxide → HCID 23323151, compound

HRID 280035Notes

Reaction equation

HRID 280035 reaction equation
[H-].[Na+].[H][H].[Cl:5][C:6]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:7]=1[C:8]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)=O.[CH3:24]S(C)=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([C:8]([C:7]2[CH:17]=[CH:18][C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:6]=2[Cl:5])=[CH2:24])=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 24758Sodium hydrideHCID 8862964-Chlorophenyl 2-chloro-4-nitrophenyl ketoneHCID 178418361HCID 178418361, compound

Product 1

HCID 23323151HCID 23323151, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 962WaterSolvent

Procedure

To 2.5 g (0.06 mole) of 60% commercial sodium hydride was added 50 ml of sieve-dried dimethylsulfoxide. The stirring mixture was heated until evolution of hydrogen gas ceased. The mixture was cooled in an ice-box and 21.4 g (0.06 mole) of (methyl)triphenylphosphonium bromide, a Wittig reagent, dissolved in 60 ml of sieve-dried dimethylsulfoxide, was added in a few minutes. The resulting mixture was stirred for 15 minutes at room temperature. Then, 9 g (0.03 mole) of 2,4'-dichloro-4-nitrobenzophenone was added as a solid. The resulting mixture was heated at 75°-80° under nitrogen overnight. The reaction mixture was diluted with 200 ml of water and extracted with ether. The ethereal extract was dried over magnesium sulfate. The extract was evaporated to dryness. The residue was dissolved in 30 ml of methylene chloride and the solution put through a silica gel column (5.5×21 cm) with an eluant of methylene chloride/n-hexane. The selected fractions were combined and evaporated to give 2.35 g of 1-(4-chlorophenyl)-1-(2-chloro-4-nitrophenyl)ethylene.

Workup

  1. temperatureThe mixture was cooled in an ice-box
  2. additionwas added in a few minutes
  3. temperatureThe resulting mixture was heated at 75°-80° under nitrogen overnight
  4. extractionextracted with ether
  5. extractionThe ethereal extract
  6. dry with materialwas dried over magnesium sulfate
  7. customThe extract was evaporated to dryness
  8. dissolutionThe residue was dissolved in 30 ml of methylene chloride
  9. customevaporated

Sources & evidence

ORD record
ord-c01132ae4b7945738ef205ab88f33d00
Source dataset
uspto-grants-1986_05
Patent number
US04587361

Reaction notes

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