m-Chloroperbenzoic acid → Methyl 3-fluoro-2-methylsulphonylbenzoate

HRID 1491581Notes

Reaction equation

HRID 1491581 reaction equation
[F:1][C:2]1[C:3](SC)=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].Cl[C:15]1C=CC=C(C(OO)=O)C=1.[S:25](S([O-])=O)([O-:28])(=O)=[O:26].[Na+].[Na+]>ClCCl>[F:1][C:2]1[C:3]([S:25]([CH3:15])(=[O:28])=[O:26])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 656671Sodium PyrosulfiteHCID 18953297Methyl 3-fluoro-2-(methylthio)benzoate

Product 1

HCID 18953324Methyl 3-fluoro-2-methylsulphonylbenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of methyl 3-fluoro-2-methylsulphenylbenzoate (14.0 g) and 3-chloroperbenzoic acid (50-60%, 55.0 g) in dichloromethane was stirred at 25° C. for 1.5 hours. 1M Sodium metabisulphite was added and the organic phase washed with sodium bicarbonate and brine, dried over sodium sulphate, filtered and evaporated. The product was recrystallised from ethyl acetate to give 8.6 g of methyl 3-fluoro-2-methylsulphonylbenzoate as white crystals, m.p. 116.2° C.

Workup

  1. washthe organic phase washed with sodium bicarbonate and brine
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customThe product was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-97a009b276364dcc8a1f7d05e2ee5542
Source dataset
uspto-grants-1994_12
Patent number
US05371064

Reaction notes

Loading…