Reaktion #660078

Reaktionsgleichung

dimethylsulfoxonium

3-bromophenylacetic acid methyl ester

4-mercaptopyridine

→

(3-Bromophenyl)(pyridin-4-ylsulfanyl)acetic acid methyl ester

Lösungsmittel

dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture is refluxed overnight
2. 2
   Einengenthen concentrated to dryness under reduced pressure
3. 3
   SonstigeThe residue is purified by chromatography on silica gel (heptane/ethyl acetate 1/1)

Vorschrift

To a solution of dimethylsulfoxonium ylide and 3-bromophenylacetic acid methyl ester (example 530E, 3 g) in dichloroethane (50 mL) are added 4-mercaptopyridine (2 equivalents) and [Ir(COD)Cl]2 (20 mg). The reaction mixture is refluxed overnight then concentrated to dryness under reduced pressure. The residue is purified by chromatography on silica gel (heptane/ethyl acetate 1/1) to give (3-Bromophenyl)(pyridin-4-ylsulfanyl)acetic acid methyl ester. 1H NMR: 8.50-8.35 (m, 2H), 7.68 (s, 1H), 7.55-7.45 (m, 2H), 7.35-7.20 (m, 1H), 7.20-7.05 (m, 2H), 5.08 (s, 1H), 3.77 (s, 3H).

Quelle