Benzyl phenyl sulphide → Benzyl phenyl sulfoxide

HRID 650939Notes

Reaction equation

HRID 650939 reaction equation
[C:1]1([S:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:23])C=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]1([S:7]([CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[O:23])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 13255Benzyl phenyl sulphideHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 239581Benzyl phenyl sulfoxideYield 110.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl phenyl sulfide (Aldrich; 1.068 g, 5.33 mmol) in 25 mL of CH2Cl2 at −78° C. was slowly added a solution of m-chloroperbenzoic acid (Aldrich, 50-60%; 760 mg, 2.64 mmol if 60%) in 10 mL of CH2CL2. After warming to room temperature and stirring overnight, the solution was added to 20 mL of a saturated NaHCO3 solution. The aqueous layer was separated and extracted with CH2Cl2 (2×10 mL). The pooled organic layers were then dried (MgSO4) and concentrated. The residue was subjected to flash column chromatography (silica gel, 10% acetone/hexane and 15% acetone/hexane) affording the sulfoxide (632 mg, 55%) as a white solid, mp 123-126° C.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with CH2Cl2 (2×10 mL)
  3. dry with materialThe pooled organic layers were then dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-aa269e45cf0a4dc79824a237ba086798
Source dataset
uspto-grants-2001_08
Patent number
US06277838B1

Reaction notes

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