3-Fluorophenol → 4-Tert-butyl-3-fluorophenol

HRID 1438376Notes

Reaction equation

HRID 1438376 reaction equation
[C:1](OC)([CH3:4])([CH3:3])[CH3:2].[F:7][C:8]1[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1>C(Cl)Cl.[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4]>[C:1]([C:13]1[CH:12]=[CH:11][C:10]([OH:14])=[CH:9][C:8]=1[F:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 97433-FluorophenolHCID 15413tert-Butyl methyl ether

Product 1

HCID 205834244-Tert-butyl-3-fluorophenolYield 51%

Reagents, catalysts & solvents 2

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-CatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Zirconiumtetrachloride (11.7 g, 50 mmol) in DCM (130 ml), tert-butylmethylether (4.44 g, 50 mmol), and 3-fluorophenol (5.6 g, 50 mmol) were mixed at room temperature and the reaction mixture was stirred for 2 hours at 50° C. The reaction was quenched with water and the whole was extracted with ethylacetate and dried over magnesium sulfate. After filtration, evaporation gave a crude residue, which was purified by silica gel column chromatography, eluting with gradually from hexane only to hexane/ethylacetate (9:1), to afford 4.25 g (51% yield) of the title compound as white solids.

Workup

  1. customThe reaction was quenched with water
  2. extractionthe whole was extracted with ethylacetate
  3. dry with materialdried over magnesium sulfate
  4. filtrationAfter filtration, evaporation
  5. customgave a crude residue, which
  6. customwas purified by silica gel column chromatography
  7. washeluting with gradually from hexane only to hexane/ethylacetate (9:1)

Sources & evidence

ORD record
ord-d1fc3123908a41b7b341037b6214df73
Source dataset
uspto-grants-2009_11
Patent number
US07622589B2

Reaction notes

Loading…