1,3-Dibromopropane → 4-[(3-Bromopropyl)sulfanyl]benzonitrile

HRID 857187Notes

Reaction equation

HRID 857187 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([SH:9])=[CH:5][CH:4]=1)#[N:2].[Br:10][CH2:11][CH2:12][CH2:13]Br.C([O-])([O-])=O.[K+].[K+]>CC#N>[Br:10][CH2:11][CH2:12][CH2:13][S:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 5850584-Thiobenzonitrile

Product 1

HCID 218676714-[(3-Bromopropyl)sulfanyl]benzonitrileYield 62.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-cyanothiophenol (20.8 g, 154 mmol), 1,3-dibromopropane (155 g, 0.77 mol) and K2CO3 (21.3 g, 154 mmol) in MeCN (300 mL) was refluxed overnight. Filtration and evaporation of the solvent gave a brown oil that crystallised when treated with EtOH. The crystals were isolated by filtration to give the sub-title compound (24.5 g, 62%).

Workup

  1. temperaturewas refluxed overnight
  2. filtrationFiltration and evaporation of the solvent
  3. customgave a brown oil that
  4. customcrystallised when
  5. additiontreated with EtOH
  6. customThe crystals were isolated by filtration

Sources & evidence

ORD record
ord-a846d75cc5364823b7042d00c385c354
Source dataset
uspto-grants-2006_12
Patent number
US07144914B2

Reaction notes

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