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

HRID 2376933Notes

Reaction equation

HRID 2376933 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

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, CDCl3): 7.27-7.22 (4H, m), 2.85 (2H, t, J 7.6), 2.30 (2H, t, J 7.6).

Workup

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

Sources & evidence

ORD record
ord-82425e37651b4b07ae1c536efa25a17a
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

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