m-Chloroperbenzoic acid → HCID 18470274, compound

HRID 2228901Notes

Reaction equation

HRID 2228901 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1.C(=O)=[O:18].CC(C)=O.ClC1C=CC=C(C(OO)=O)C=1.S([O-])([O-])=O.[Na+].[Na+].C(=O)([O-])O.[Na+]>ClCCl>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)=[O:18]

Participants

6

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 18470318HCID 18470318, compoundHCID 18470521Sodium bicarbonate sodium sulfiteHCID 18522661Acetone cardice

Product 1

HCID 18470274HCID 18470274, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-bromo-7-(4-chlorophenylthio)heptane (0.80 g) in dichloromethane (10 ml) was cooled to −78° C. (cardice/acetone) and a slurry of metachloroperbenzoic acid (60%, 0.72 g) in dichloromethane (5 ml) was added over 20min. After 40 min, the reaction was allowed to warm to room temperature and shaken with aqueous sodium sulfite/sodium hydrogen carbonate solution. The organic layer was dried over magnesium sulfate and evaporated under reduced pressure. The residue was chromatographed on silica gel using dichloromethane to 4% methanol in dichloromethane as eluents to give 1-bromo-7-(4-chlorophenylsulfinyl)heptane (0.43 g). 1H-NMR (CDCl3) δ 1.2-2.0 (10H, m), 2.77 (2H, t), 3.39 (2H, t) and 7.4-7.7 (4H, m).

Workup

  1. dry with materialThe organic layer was dried over magnesium sulfate
  2. customevaporated under reduced pressure
  3. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-54f2ecfea6dc44a994bef646c9b53116
Source dataset
uspto-grants-2002_07
Patent number
US06417192B1

Reaction notes

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