m-Chloroperbenzoic acid → HCID 18470393, compound

HRID 2228902Notes

Reaction equation

HRID 2228902 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]SC1C=CC(Cl)=CC=1.[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20](C(OO)=O)[CH:19]=1.[S:28]([O-:31])([O-])=[O:29].[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:28]([C:21]1[CH:20]=[CH:19][C:18]([Cl:17])=[CH:23][CH:22]=1)(=[O:31])=[O:29]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 18470318HCID 18470318, compoundHCID 18470521Sodium bicarbonate sodium sulfite

Product 1

HCID 18470393HCID 18470393, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1 -bromo-7-(4-chlorophenylthio)heptane (1.19 g) in dichloromethane (20 ml) at −20° C. was added metachloroperbenzoic acid (60%, 2.23 g) portionwise over 15 min. The mixture was allowed to warm to room temperature over 1 h and was 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 50:50 hexane:dichloromethane as eluent to give 1-bromo-7-(4-chlorophenylsulfonyl)heptane (1.17 g). 1H-NMR (CDCl3) δ 1.2-2.0 (10H, m), 3.07 (2H, m), 3.38 (2H, t), 7.5-7.6 (2H, m) and 7.8-7.9 (2H, 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 using 50:50 hexane

Sources & evidence

ORD record
ord-9ab8da5369de4572be6f926f7983d312
Source dataset
uspto-grants-2002_07
Patent number
US06417192B1

Reaction notes

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