4-Fluorophenol → 2-(4-Fluorophenoxy)thiophene

HRID 2082092Notes

Reaction equation

HRID 2082092 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[C:10]1[S:11][CH:12]=[CH:13][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1.[Cu]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 138512-Bromothiophene

Product 1

HCID 197795412-(4-Fluorophenoxy)thiopheneYield 9.4%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1049PyridineSolvent

Procedure

A solution of 4-fluorophenol (22.42 g, 200 mmol), 2-bromothiophene (65.22 g, 400 mmol), potassium carbonate (42.84 g, 310 mmol), and copper powder (6.35 g, 100 mmol) in pyridine (200 mL) was refluxed for 18 hours. It was then cooled to ambient temperature and filtered through Celite. The filtrate was diluted with ethyl acetate (500 mL) and washed with water (3×300 mL). The organic phase was dried over MgSO4 and concentrated. The resulting residue was chromatographed (silica gel; hexanes) to afford 3.67 g (9%) of 2-(4-fluorophenoxy)thiophene as a colorless oil.

Workup

  1. filtrationfiltered through Celite
  2. additionThe filtrate was diluted with ethyl acetate (500 mL)
  3. washwashed with water (3×300 mL)
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated
  6. customThe resulting residue was chromatographed (silica gel; hexanes)

Sources & evidence

ORD record
ord-43d42fe6ef37402582111bf0f1e81b6e
Source dataset
uspto-grants-1993_02
Patent number
US05187192

Reaction notes

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