Phenol → 2-Phenoxy-5-trifluoromethyl-phenol

HRID 1822330Notes

Reaction equation

HRID 1822330 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[O:12]C.[C:14]1([OH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[O:20]([C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:9])([F:10])[F:11])=[CH:4][C:3]=1[OH:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 27747712-Fluoro-5-(trifluoromethyl)anisole

Product 1

HCID 578942142-Phenoxy-5-trifluoromethyl-phenolYield 51.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 4-fluoro-3-methoxybenzotrifluoride (5.26 g, 28.9 mmol), phenol (2.71 g, 28.8 mmol) and 325 mesh potassium carbonate (4.79 g, 34.7 mmol) in dry DMSO (50 mL) is heated to 130° C. and stirred for 17 hours under N2. The reaction is filtered, and the filtrate is acidified with 1 N HCl. The mixture is diluted with water and extracted with Et2O. The organic layer is dried (Na2SO4), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using 15/1 hexanes/ethyl acetate to afford 3.79 g (49%) of the title compound (Rf=0.47 (4/1 hexanes/EtOAc) that is contaminated with starting 4-fluoro-3-methoxybenzotrifluoride.

Workup

  1. filtrationThe reaction is filtered
  2. additionThe mixture is diluted with water
  3. extractionextracted with Et2O
  4. dry with materialThe organic layer is dried (Na2SO4)
  5. customthe solvent is removed in vacuo
  6. customto afford crude product that
  7. customis absorbed on silica gel
  8. custompurified by flash chromatography

Sources & evidence

ORD record
ord-390ba6e598a747e2a050211a4122f307
Source dataset
uspto-grants-2009_10
Patent number
US07608639B2

Reaction notes

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