HCID 68529627, compound → 2-[(4-Fluorophenyl)methyl]phenol

HRID 2108665Notes

Reaction equation

HRID 2108665 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH:3]=1.CC1C=C(C=C(C)C=1CC1C=CC(OCOC)=C(CC2C=CC(F)=CC=2)C=1)C(OC)=O>[Pd].CO>[F:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][C:4]2[CH:3]=[CH:2][CH:7]=[CH:6][C:5]=2[OH:8])=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 68529627HCID 68529627, compoundHCID 68530716HCID 68530716, compound

Product 1

HCID 2584312-[(4-Fluorophenyl)methyl]phenolYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-bromo-2-(4-fluorobenzyl)phenol (compound 78, step a, 6.0 gm, 21.4 mmol), 1.2 g of palladium on activated carbon (10%) and 100 mL of methanol in a glass reaction vessel was shaken at 50 psi H2 over night, filtered and concentrated under reduced pressure. The resulting light orange oil was dissolved in 180 mL dichloromethane and washed 1× with NaHCO3 saturated solution. The organic was dried over Na2SO4, filtered and concentrated under reduced pressure to afford 2-(4-fluorobenzyl)phenol (4.52 gm, 100%): 1H NMR (200 MHz, DMSO-d6): δ 9.39 (s, 1H), 7.22 (m, 2H), 7.02 (m, 3H), 6.74 (m, 2H), 3.84 (s, 2H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=methylene chloride-hexanes (1:1); Rf=0.32.

Workup

  1. customin a glass reaction vessel
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe resulting light orange oil was dissolved in 180 mL dichloromethane
  5. washwashed 1× with NaHCO3 saturated solution
  6. dry with materialThe organic was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dcd6a7e5491342eeaba4aa174df006a9
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

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