4-bromo-N,N-dimethylaniline → HCID 375377, compound

HRID 725289Notes

Reaction equation

HRID 725289 reaction equation
[CH3:1][N:2]([CH3:10])[C:3]1[CH:8]=[CH:7][C:6](Br)=[CH:5][CH:4]=1.[Mg].[S:12](Cl)(Cl)=[O:13]>C1COCC1>[CH3:1][N:2]([CH3:10])[C:3]1[CH:8]=[CH:7][C:6]([S:12]([C:6]2[CH:7]=[CH:8][C:3]([N:2]([CH3:10])[CH3:1])=[CH:4][CH:5]=2)=[O:13])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 114654-bromo-N,N-dimethylanilineHCID 24386Thionyl ChlorideHCID 5462224Magnesium

Product 1

HCID 375377HCID 375377, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A Grignard reagent was conventionally prepared using 4-dimethylaminophenyl bromide, magnesium, and THF and further reacted with thionyl chloride, obtaining bis(4-dimethylaminophenyl) sulfoxide in a yield of 33%. A solution of 7.0 g (0.024 mol) of the thus obtained bis(4-dimethylaminophenyl) sulfoxide in 100 g of methylene chloride was cooled at -70° C. in a dry ice/methanol bath whereupon with stirring, 6.0 g (0.027 mol) of trimethylsilyl triflate was added dropwise thereto at less -60° C.

Sources & evidence

ORD record
ord-2ec864d9134b4739ba7499f18b169e28
Source dataset
uspto-grants-1998_01
Patent number
US05705702

Reaction notes

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