2-Iodophenol → HCID 11279266, compound

HRID 2355377Notes

Reaction equation

HRID 2355377 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].F[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-:18])=[O:17].C([O-])([O-])=O.[K+].[K+].[F-].[Cs+]>CS(C)=O>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-:18])=[O:17]

Participants

6

Reactant 4

HCID 107842-IodophenolHCID 11430Potassium CarbonateHCID 25953Cesium fluorideHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 11279266HCID 11279266, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-iodophenol (11.82 g, 52.7 mmol) and 1-fluoro-2-nitrobenzene (5.0 g, 35.1 mmol) in DMSO (50 mL was added K2CO3 (14.5 g, 105.3 mmol), followed by CsF (8.0 g, 52.7 mmol). The resulting suspension was stirred at 50° C. until no starting material remained (˜5 h), cooled to rt and partitioned between water (50 mL) and CH2Cl2 (50 mL). The water layer was separated and extracted with CH2Cl2 (2×10 mL). The combined organic layers were washed with 1 aq N NaOH (10 mL) and brine, and dried over Na2SO4. Solvent was removed under vacuum to give 1-(2-iodophenoxy)-2-nitrobenzene (11.2 g, 93%) as an oil, which was used for next step without purification.

Workup

  1. custom(˜5 h)
  2. temperaturecooled to rt
  3. custompartitioned between water (50 mL) and CH2Cl2 (50 mL)
  4. customThe water layer was separated
  5. extractionextracted with CH2Cl2 (2×10 mL)
  6. washThe combined organic layers were washed with 1 aq N NaOH (10 mL) and brine
  7. dry with materialdried over Na2SO4
  8. customSolvent was removed under vacuum

Sources & evidence

ORD record
ord-2e8e1ceb28724a3abf2ada73a0e1e6d2
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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