Dimethyl Sulfoxide → HCID 69880397, compound

HRID 1008270Notes

Reaction equation

HRID 1008270 reaction equation
[CH2:1](P(=O)([O-])OCC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C1C=C[C:20]([Br:23])=[CH:19][CH:18]=1)=O.[CH3:24]S(C)=O.[CH3:28][C:29]([CH3:32])([O-])[CH3:30].[K+]>C(OCC)(=O)C.O>[Br:23][C:20]1[CH:28]=[C:29]([C:32]([CH3:24])=[CH:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:30]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 7466p-BromoacetophenoneHCID 23421887HCID 23421887, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 69880397HCID 69880397, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 500 ml flask, 23 g(0.1 mol) of ethyl benzylphosphonate, 20 g (0.1 mol) of 4-bromoacetophenone and 200 ml of dimethyl sulfoxide were placed and cooled at 0° C. with ice water. Then, 13.4 g (0.12 mol) of potassium t-butoxide was slowly added and the resultant mixture was kept being stirred at the room temperature for one night. After the reaction was completed, the reaction solution was poured into 500 ml of water and the organic layer was treated by extraction with ethyl acetate. After drying with magnesium sulfate, the organic layer was concentrated in vacuo using a rotary evaporator. The obtained product were purified in accordance with the column chromatography (silica gel; the developing solvent: hexane) and 26 g (the yield: 88%) of 3-bromo-α-methylstilbene as the object compound was obtained.

Workup

  1. dry with materialAfter drying with magnesium sulfate
  2. concentrationthe organic layer was concentrated in vacuo
  3. customa rotary evaporator
  4. customThe obtained product were purified in accordance with the column chromatography (silica gel

Sources & evidence

ORD record
ord-37e6f77afb3b497998276ed614a0e1fc
Source dataset
uspto-grants-2004_09
Patent number
US06797848B2

Reaction notes

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