Potassium Hydroxide → 2-(Benzyloxy)-3-fluorophenol

HRID 39016Notes

Reaction equation

HRID 39016 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=1Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:17]1CCOCC1.[OH-].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH2:1]([O:8][C:9]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=1[OH:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 312751,4-DioxaneHCID 532169822-(Benzyloxy)-1-chloro-3-fluorobenzene

Product 1

HCID 107751752-(Benzyloxy)-3-fluorophenol

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-(benzyloxy)-1-chloro-3-fluorobenzene (3 g, 12.71 mmol), dioxane (6 ml), KOH (0.78 g, 14 mmol), water (6 ml), Tris(dibenzylideneacetone)dipalladium (0.12 g, 0.13 mmol) and 2-di-tertbutylphosphine-2,4,6-triisopropylbiphenyl (0.22 g, 0.51 mmol) was flushed with N2 and heated under microwave radiation at 120° C. for 7 min. HCl (1 N) was added and the solution was extracted with EtOAc. The combined organic phases were dried (Na2SO4) and evaporated to dryness. Flash column chromatography (isooctane/EtOAc) yielded the title compound (1.86 g). MS m/z (rel. intensity, 70 eV) 218 (M+, 4), 92 (8), 91 (bp), 65 (13), 51 (9).

Workup

  1. customwas flushed with N2
  2. additionHCl (1 N) was added
  3. extractionthe solution was extracted with EtOAc
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-9ab18781cc814d62921fc9a44e38d60c
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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