Water → Benzonitrile, 2-(4-bromophenoxy)-5-nitro-

HRID 1155733Notes

Reaction equation

HRID 1155733 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[OH-].[Na+].Cl[C:12]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:13]=1[C:14]#[N:15].O>CS(C)=O.C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:12]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:13]=2[C:14]#[N:15])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 78084-BromophenolHCID 14798Sodium HydroxideHCID 855042-Chloro-5-nitrobenzonitrile

Product 1

HCID 514841Benzonitrile, 2-(4-bromophenoxy)-5-nitro-Yield 85.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5.31 g (0.0307 moles) of 4-bromophenol dissolved in 150 ml of DMSO was added 1.23 g (0.0307 moles) of NaOH. The slurry was heated at 60° C. for 15 minutes and 5.04 g (0.0276 moles) of 2-chloro-5-nitrobenzonitrile was added. The mixture was heated at 75° C. for 4 hrs. The reaction mixture was cooled and poured into water. The product was collected by filtration, washed well with water and dried, which gave 8.1 g of crude product. The crude product was dissolved in CH2Cl2 and washed with 10% aqueous NaOH, water and dried (Na2SO4). Removal of solvent in vacuo gave 7.5 g (85% yield) of product. Recrystallization from ethanol afforded purified 2-(4-bromophenoxy)-5-nitrobenzonitrile, mp 171°-172° C.

Workup

  1. temperatureThe mixture was heated at 75° C. for 4 hrs
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe product was collected by filtration
  4. washwashed well with water
  5. customdried
  6. customwhich gave 8.1 g of crude product
  7. washwashed with 10% aqueous NaOH, water
  8. dry with materialdried (Na2SO4)
  9. customRemoval of solvent in vacuo

Sources & evidence

ORD record
ord-fc87d45751094fa8a4fbf09b7daea3c5
Source dataset
uspto-grants-1982_06
Patent number
US04332820

Reaction notes

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