Pyridine → toluene-4-sulfonic acid (S)-2-(3-bromophenyl)-2-fluoro-ethyl ester

HRID 30602Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 30602
[F:1][C@H:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[CH:6]=1)[CH2:3][OH:4].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.N1C=CC=CC=1>C(Cl)Cl>[Br:11][C:7]1[CH:6]=[C:5]([C@H:2]([F:1])[CH2:3][O:4][S:18]([C:15]2[CH:16]=[CH:17][C:12]([CH3:22])=[CH:13][CH:14]=2)(=[O:20])=[O:19])[CH:10]=[CH:9][CH:8]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 68649207(R)-2-fluoro-2-(3-bromophenyl)-1-ethanol

Produkt 1

HCID 59790335toluene-4-sulfonic acid (S)-2-(3-bromophenyl)-2-fluoro-ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of (R)-2-fluro-2-(3-bromophenyl)-1-ethanol (5 mmol) and p-toluenesulfonyl chloride (5.1 mmol) in CH2Cl2 at ice bath temperatures is treated with stirring with pyridine. The reaction mixture is heated at reflux temperature under a nitrogen atmosphere for 16 h, cooled to room temperature, washed with 10% HCl, saturated NaHCO3 and brine, dried over MgSO4 and concentrated in vacuo to give toluene4-sulfonic acid (S)-2-(3-bromophenyl)-2-fluoro-ethyl ester.

Aufarbeitung

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux temperature under a nitrogen atmosphere for 16 h
  3. washwashed with 10% HCl, saturated NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1cf5de85ee4f4b5abaf2be9987915ebf
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423158B2

Notizen zur Reaktion

Wird geladen…