Acetic Acid → 3-((4-Bromophenyl)sulfonyl)propanenitrile

HRID 1351618

Reaktionsgleichung

Reaktionsgleichung von HRID 1351618
O.O.[Br:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.[Na+].[C:14](#[N:17])[CH:15]=[CH2:16].C(O)(=O)C>O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH2:16][CH2:15][C:14]#[N:17])(=[O:12])=[O:11])=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 7855AcrylonitrileHCID 23683129Sodium 4-bromobenzene-1-sulfinate--water (1/1/2)

Produkt 1

HCID 20497813-((4-Bromophenyl)sulfonyl)propanenitrileAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a suspension of sodium 4-bromophenylsulfinate dihydrate (130 g, 0.53 mol) in water (600 mL) was added acrylonitrile (70 mL, 1.07 mol) and acetic acid (62 mL, 1.07 mol). The reaction was stirred for 1.5 h at 100° C. then cooled to room temperature. The solid was filtered off, washed thoroughly with water and dried over P2O5 to give 3-[(4-bromophenyl)sulfonyl]propanenitrile (125 g). δH (400 MHz, CDCl3): 7.27–7.22 (4H, m), 2.85 (2H, t, J 7.6), 2.30 (2H, t, J 7.6).

Aufarbeitung

  1. temperaturethen cooled to room temperature
  2. filtrationThe solid was filtered off
  3. washwashed thoroughly with water
  4. dry with materialdried over P2O5

Quellen und Nachweise

ORD-Eintrag
ord-30054fec09ff41c79974f43873470f96
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07217740B2

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