Sodium Iodide → 4-(4-Hydroxy-3-iodophenyl)benzonitrile

HRID 1064651Notes

Reaction equation

HRID 1064651 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[I-:16].[Na+].[OH-].[Na+].Cl[O-].[Na+].P([O-])(O)(O)=O.[Na+]>CO.S([O-])([O-])(=O)=S.[Na+].[Na+].O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:6][C:7]=1[I:16]

Participants

9

Reactant 5

HCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 1406104'-Hydroxy-4-biphenylcarbonitrileHCID 23665760Sodium HypochloriteHCID 23672064Monosodium phosphate

Product 1

HCID 103586764-(4-Hydroxy-3-iodophenyl)benzonitrileYield 53%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

To a solution of 4-hydroxy-4′-cyanobiphenyl (6.00 g, 30.8 mmol), sodium iodide (4.61 g, 30.8 mmol) and sodium hydroxide (1.23 g, 30.8 mmol) in methanol (90 mL) at 0° C. was added an aqueous solution of sodium hypochlorite (47 mL of 5.25% Clorox™, 2.29 g, 30.8 mmol) over 45 minutes. The mixture was stirred cold for 1 hour, warmed to ambient temperature and diluted with sodium thiosulfate solution (10 mL), water (80 mL) and adjusted to a pH of 7 by addition of sodium dihydrogen phosphate. The mixture was extracted with dichloromethane (2×90 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure to give a white powder. The solid was crystallized from dichloroethane/hexane and chromatographed on silica with dichloromethane to give the titled compound (5.19 g, 53%). MS (DCI) m/z 339[M+NH4+]+;

Workup

  1. extractionThe mixture was extracted with dichloromethane (2×90 mL)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto give a white powder
  6. customThe solid was crystallized from dichloroethane/hexane
  7. customchromatographed on silica with dichloromethane

Sources & evidence

ORD record
ord-2749cd05e02e474a99e6ee4eb443b3af
Source dataset
uspto-grants-2005_11
Patent number
US06969730B2

Reaction notes

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