Dimethyl Sulfoxide → 9-Bromo-10-(4-(2-phenylvinyl)phenyl)anthracene

HRID 901765Notes

Reaction equation

HRID 901765 reaction equation
[Br:1][C:2]1[C:3]2[C:8]([C:9]([C:16]3[CH:21]=[CH:20][C:19]([CH:22]=O)=[CH:18][CH:17]=3)=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[CH2:24](P(=O)(OCC)OCC)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CS(C)=O.CC(C)([O-])C.[K+]>O>[Br:1][C:2]1[C:3]2[C:8]([C:9]([C:16]3[CH:21]=[CH:20][C:19]([CH:22]=[CH:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:18][CH:17]=3)=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 14122Diethyl benzylphosphonateHCID 22138045HCID 22138045, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 738668529-Bromo-10-(4-(2-phenylvinyl)phenyl)anthraceneYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under an atmosphere of argon, 9-bromo-10-(4-formylphenyl)-anthracene (3.9 g, 11 mmole) and diethyl benzylphosphonate (3 g, 13 mmole, 1.2 eq) were suspended into DMSO (25 ml). To the resultant suspension, potassium t-butoxide (1.6 g, 14 mmole, 1.1 eq) was added and the obtained mixture was stirred at the room temperature for 10 hours and left standing for one night. The reaction mixture was diluted with water (50 ml) and subjected to extraction with toluene (300 ml). The organic layer was washed with water (50 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 yellow solid was obtained. The obtained solid was purified by recrystallization from toluene (40 ml) and yellow needle crystals (4.1 g, 86%) were obtained.

Workup

  1. waitleft
  2. waitstanding for one night
  3. extractionsubjected to extraction with toluene (300 ml)
  4. washThe organic layer was washed with water (50 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 yellow solid was obtained
  8. customThe obtained solid was purified by recrystallization from toluene (40 ml)

Sources & evidence

ORD record
ord-6e46fa1d8f5e40e9a5da7f75547d19ca
Source dataset
uspto-grants-2008_04
Patent number
US07361796B2

Reaction notes

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