HCID 21556730, compound → HCID 21556745, compound

HRID 267299Notes

Reaction equation

HRID 267299 reaction equation
[O-:1]I(=O)(=O)=O.[Na+].[CH3:7][S:8][C:9]1[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[C:12]([Br:18])=[CH:11][C:10]=1[CH:19]([CH3:21])[CH3:20]>O.CO.CC(C)=O>[CH3:7][S:8]([C:9]1[CH:14]=[C:13]([CH:15]([CH3:16])[CH3:17])[C:12]([Br:18])=[CH:11][C:10]=1[CH:19]([CH3:21])[CH3:20])=[O:1]

Participants

6

Reactant 2

HCID 21556730HCID 21556730, compoundHCID 23667635Sodium periodate

Product 1

HCID 21556745HCID 21556745, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

4-Bromo-2,5-diisopropylphenyl methyl sulfoxide was prepared as follows: A solution of 25.7 g of sodium m-periodate in 200 ml of water was added portionwise over 0.5 hour to 31.9 g of 4-bromo-2,5-diisopropylphenyl methyl sulfide (prepared in Example 1C) in 200 ml of methanol and 350 ml of acetone at ambient temperature. After stirring for 16 hours, the reaction mixture was filtered and the solid portion was extracted with chloroform. The filtrate was diluted with 1 liter of water and the solid residue that formed was collected on a filter. The second residue was extracted with chloroform. The two chloroform extracts were combined, washed with half-saturated sodium chloride solution, and dried over sodium sulfate. Removal of the chloroform gave a pale-yellow product containing some sulfide which was removed by recrystallization from n-hexane to give pure 4-bromo-2,5-diisopropylphenyl methyl sulfoxide which softened at 110°C and melted at 114°-117°C [Ʊ(S=O) 9.6μ].

Workup

  1. custom4-Bromo-2,5-diisopropylphenyl methyl sulfoxide was prepared
  2. filtrationthe reaction mixture was filtered
  3. extractionthe solid portion was extracted with chloroform
  4. additionThe filtrate was diluted with 1 liter of water
  5. customthe solid residue that formed
  6. customwas collected on a filter
  7. extractionThe second residue was extracted with chloroform
  8. washwashed with half-saturated sodium chloride solution
  9. dry with materialdried over sodium sulfate
  10. customRemoval of the chloroform
  11. customgave a pale-yellow product
  12. customwas removed by recrystallization from n-hexane

Sources & evidence

ORD record
ord-3e5f0e7bdda741cbbd96713499ae4618
Source dataset
uspto-grants-1976_03
Patent number
US03941826

Reaction notes

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