4-Fluorophenol → HCID 67757880, compound

HRID 744704Notes

Reaction equation

HRID 744704 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][CH:6]=1)[CH:2]=[CH2:3].[F:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1.[Cu]>[F:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH:3]=[CH:2][CH2:1][O:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 2579441-Bromo-4-[(prop-2-en-1-yl)oxy]benzene

Product 1

HCID 67757880HCID 67757880, compoundYield 49.1%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1049PyridineSolvent

Procedure

A solution of 4-allyloxybromobenzene (42.24 g, 198.3 mmol), 4-fluorophenol (14.82 g, 132.2 mmol), potassium carbonate (27.41 g, 198.3 mmol) and copper (4.20 g, 66.1 mmol) in pyridine (200 mls) was refluxed for 2 days. It was then filtered through Celite and diluted with ethylacetate(500 mls). The organic was then washed with water (3×200 mls), dried with MgSO4 and concentrated. The resulting residue was chromatographed (silica gel, hexanes:ether, 99.75:0.25) to afford 15.85 g (49%) of 4-(4-fluorophenoxy)allyloxybenzene as a lemon yellow oil.

Workup

  1. filtrationIt was then filtered through Celite
  2. additiondiluted with ethylacetate(500 mls)
  3. washThe organic was then washed with water (3×200 mls)
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated
  6. customThe resulting residue was chromatographed (silica gel, hexanes:ether, 99.75:0.25)

Sources & evidence

ORD record
ord-623225489bbb4adabd0736df394c1f42
Source dataset
uspto-grants-1996_09
Patent number
US05559144

Reaction notes

Loading…