2,5-Dichlorophenol → HCID 29042269, compound

HRID 1877377Notes

Reaction equation

HRID 1877377 reaction equation
I[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[OH:19].C(=O)([O-])[O-].[Cs+].[Cs+].Cl>C1(C)C=CC=CC=1.O.CC#N.CC#N.CC#N.CC#N.F[P-](F)(F)(F)(F)F.[Cu+]>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[O:19][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

8

Reactant 4

HCID 662,5-DichlorophenolHCID 313Hydrochloric AcidHCID 69412-Iodobenzoic acidHCID 10796Cesium carbonate

Product 1

HCID 29042269HCID 29042269, compound

Reagents, catalysts & solvents 3

HCID 11068737tetrakis(acetonitrile)copper(I) hexafluorophosphateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of 2-iodo-benzoic acid (3.0 g, 12.10 mmol, 1.0 equiv; [CAS RN 88-67-5]) and 2,5-dichloro-phenol (1.97 g, 12.10 mmol, 1.0 equiv; [CAS RN 583-78-8]) in toluene (50 mL) was added caesium carbonate (7.88 g, 24.20 mmol, 2.0 equiv; [CAS RN 534-17-8]) and tetrakis(acetonitrile)copper(I) hexafluorophosphate (1.13 g, 3.02 mmol, 0.25 equiv; [CAS RN 64443-05-6]). The reaction mixture was heated to reflux over night. The solvent was evaporated under reduced pressure and the crude reaction product taken up in water (100 mL), acidified to pH 1 by addition of a solution of 1 M HCl and extracted with ethyl acetate (3×100 mL). The combined organic phases were dried over MgSO4 and the product purified by silica column chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of heptane (+1% acetic acid)/ethyl acetate affording 2.78 g (81%) of the title compound as a white solid. MS (ISN): 281.1 [M−H]−.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux over night
  3. customThe solvent was evaporated under reduced pressure
  4. customthe crude reaction product
  5. extractionextracted with ethyl acetate (3×100 mL)
  6. dry with materialThe combined organic phases were dried over MgSO4
  7. customthe product purified by silica column chromatography
  8. washeluting with a gradient of heptane (+1% acetic acid)/ethyl acetate affording 2.78 g (81%) of the title compound as a white solid

Sources & evidence

ORD record
ord-3e595f77645b4d299a4bcbd25d1d7ba2
Source dataset
uspto-grants-2012_11
Patent number
US08309734B2

Reaction notes

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