Sodium Carbonate → 4-(4-Fluorophenyl)phenethyl alcohol

HRID 533571Notes

Reaction equation

HRID 533571 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[F:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=2)=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 728512-(4-Bromophenyl)ethanolHCID 2856454-Fluorophenylboronic acid

Product 1

HCID 27591314-(4-Fluorophenyl)phenethyl alcohol

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

To a 2-5 mL microwave vial was added 2-(4-bromophenyl)ethanol (603 mg, 3.0 mmol), (4-fluorophenyl)boronic acid (462 mg, 3.3 mmol), sodium carbonate (973 mg, 9.0 mmol), palladium acetate (33.7 mg, 0.15 mmol), 1,4dioxane (4.5 mL) and water (4.5 mL). The mixture was irradiated in a CEN microwave at 120° C. for 10 minutes. The reaction mixture was biphasic upon reaction completion. The reaction mixture was extracted into ethyl acetate (2×150 mL) dried over Na2SO4 then filtered through a pad of celite. The organics were concentrated in vacuo and the crude material was purified by chromatography on silica gel (gradient: 70:30 heptanes:EtOAc). Isolated material still contained 2-(4-bromophenyl)ethanol, therefore, the material was triturated in heptanes to furnish the title compound as a white solid. (430 mg, 45%).

Workup

  1. customThe mixture was irradiated in a CEN microwave at 120° C. for 10 minutes
  2. customThe reaction mixture was biphasic upon reaction completion
  3. extractionThe reaction mixture was extracted into ethyl acetate (2×150 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationthen filtered through a pad of celite
  6. concentrationThe organics were concentrated in vacuo
  7. customthe crude material was purified by chromatography on silica gel (gradient: 70:30 heptanes:EtOAc)
  8. customIsolated material still contained 2-(4-bromophenyl)ethanol, therefore, the material was triturated in heptanes

Sources & evidence

ORD record
ord-6cb0a834f34b46cf8b228c5a983cf3cf
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

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