4-Fluorophenol → 1-(4-Fluorophenoxy)-3-methylbenzene

HRID 704815Notes

Reaction equation

HRID 704815 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.COCCOCCN(CCO[CH2:29][CH2:30]OC)CCOCCOC>BrC1C=C(C)C=CC=1.[Cu]Cl>[F:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:5]2[CH:6]=[C:29]([CH3:30])[CH:8]=[CH:9][CH:4]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 97324-FluorophenolHCID 24758Sodium hydrideHCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-

Product 1

HCID 200688011-(4-Fluorophenoxy)-3-methylbenzene

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 115603-BromotolueneSolvent

Conditions

Temperature
45 °C

Procedure

Sodium hydride (1 80 g) was suspended in 3-bromotoluene (51.3 g, Aldrich) and 4-fluorophenol (8.40 g, Aldrich) added over 1/4 hour with stirring. The mixture was then heated at 45° C. until effervescence stopped (1/2 hour). After cooling, copper(I) chloride (3.75 g) was added followed by TDA-1 (12 g) over 10 minutes with further cooling. The mixture was then heated at 180° C. under N2 for 24 hours. After cooling, the mixture was treated with 2 M aqu. HCl (100 ml) and extracted with ether. The extract was washed with 2 M aqu. HCl (2×100 ml), with 2 M aqu. NaOH and with water (2×100 ml), then treated with charcoal, filtered through Hyflo and stripped. The residue was distilled under reduced pressure to give the desired product, bp 130°-135° C./10 mm Hg.

Workup

  1. custom(1/2 hour)
  2. temperatureAfter cooling
  3. temperatureThe mixture was then heated at 180° C. under N2 for 24 hours
  4. temperatureAfter cooling
  5. additionthe mixture was treated with 2 M aqu
  6. extractionHCl (100 ml) and extracted with ether
  7. washThe extract was washed with 2 M aqu
  8. additionNaOH and with water (2×100 ml), then treated with charcoal
  9. filtrationfiltered through Hyflo
  10. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-b259423b451a4817b52991c256236fc7
Source dataset
uspto-grants-1991_01
Patent number
US04988733

Reaction notes

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