Hydrogen Bromide → (4-Methylphenyl)(diphenyl)sulfanium bromide

HRID 1989811Notes

Reaction equation

HRID 1989811 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[Mg].[C:10]1([S:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl[Si](C)(C)C.Br>O1CCCC1>[Br-:1].[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([S+:16]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:3][CH:4]=1

Participants

7

Reactant 5

HCID 260Hydrogen BromideHCID 6397ChlorotrimethylsilaneHCID 78054-BromotolueneHCID 13679Diphenyl sulfoxideHCID 5462224Magnesium

Product 1

HCID 23133059(4-Methylphenyl)(diphenyl)sulfanium bromideYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a 4-methylphenyl Grignard reagent of 1.32 L (1.88 mol, 1.42 mol/L, 2.5 equiv.) prepared by a common method from 4-bromotoluene and magnesium as raw materials using tetrahydrofuran (THF) as a solvent was added a solution dissolving diphenyl sulfoxide of 151.71 g (0.75 mol, 1 equiv.) and chlorotrimethylsilane (TMSCl) of 407.25 g (3.75 mol, 5 equiv.) in THF of 0.6 L at −5° C. to room temperature, followed by reacting under stirring for 30 minutes. After termination of the reaction, the resultant reaction mixture was poured into 12% hydrobromic acid of 1.1 L and extracted two times with dichloromethane of 1.8 L. The obtained product was washed with water and then concentrated to dryness and crystallized in acetone of 1.8 L to obtain the product of 203.7 g as a white crystal (yield: 76%). Property data thereof are shown in Table 1.

Workup

  1. additionwas added a solution
  2. customAfter termination of the reaction
  3. customthe resultant reaction mixture
  4. extractionextracted two times with dichloromethane of 1.8 L
  5. washThe obtained product was washed with water
  6. concentrationconcentrated to dryness
  7. customcrystallized in acetone of 1.8 L

Sources & evidence

ORD record
ord-09a6ed8d1669439aad458c151d7d50e2
Source dataset
uspto-grants-2010_01
Patent number
US07642368B2

Reaction notes

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