Dimethyl Sulfoxide → 1-(2,2-Diphenylvinyl)-3,5-dibromobenzene

HRID 901756Notes

Reaction equation

HRID 901756 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Br:10])[CH:9]=1)[CH:5]=O.[C:11]1([CH:17](P(=O)(OCC)OCC)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CS(C)=O.CC(C)([O-])C.[K+]>O>[C:11]1([C:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:5][C:4]2[CH:3]=[C:2]([Br:1])[CH:9]=[C:8]([Br:10])[CH:7]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6220773,5-DibromobenzaldehydeHCID 10267017Diethyl benzhydrylphosphonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 221380311-(2,2-Diphenylvinyl)-3,5-dibromobenzeneYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under an atmosphere of argon, 3,5-dibromobenzaldehyde (12.1 g, 46 mmole) and diethyl diphenylmethylphosphonate (15 g, 49 mmole, 1.1 eq) were dissolved into dimethyl sulfoxide (DMSO) (60 ml). To the resultant solution, potassium t-butoxide (6.2 g, 55 mmole, 1.2 eq) was added in small portions and the obtained solution was stirred at the room temperature for 9 hours and left standing for one night. After water (60 ml) was added, the reaction mixture was subjected to extraction with ethyl acetate (250 ml). The obtained organic layer was washed with water (100 ml) and a saturated aqueous solution of sodium chloride (50 ml) and dried with magnesium sulfate. Then, the solvent was removed by distillation and a deep brown oil was obtained. The obtained oil was purified by the column chromatography (silica gel/hexane and hexane+3% dichloromethane, successively) and a white solid (14.0 g, 74%) was obtained.

Workup

  1. waitleft
  2. waitstanding for one night
  3. extractionthe reaction mixture was subjected to extraction with ethyl acetate (250 ml)
  4. washThe obtained organic layer was washed with water (100 ml)
  5. dry with materiala saturated aqueous solution of sodium chloride (50 ml) and dried with magnesium sulfate
  6. customThen, the solvent was removed by distillation
  7. customa deep brown oil was obtained
  8. customThe obtained oil was purified by the column chromatography (silica gel/hexane and hexane+3% dichloromethane

Sources & evidence

ORD record
ord-7bb6aef65834474daca6eca4c6bfc21a
Source dataset
uspto-grants-2008_04
Patent number
US07361796B2

Reaction notes

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