1-(4-Fluoro-3-methoxyphenyl)-2-phenylethanol → 1-(4-Fluoro-3-methoxyphenyl)-2-phenylethanone

HRID 1874189Notes

Reaction equation

HRID 1874189 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:16])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][C:3]=1[O:17][CH3:18].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:16])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][C:3]=1[O:17][CH3:18]

Participants

4

Reactant 2

HCID 594588961-(4-Fluoro-3-methoxyphenyl)-2-phenylethanolHCID 131709961Jones' reagent

Product 1

HCID 594584091-(4-Fluoro-3-methoxyphenyl)-2-phenylethanoneYield 151.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1-(4-fluoro-3-methoxyphenyl)-2-phenylethanol (23.7 g, 40.6 mmol) in acetone (240 mL) was added Jones reagent (64 mL) at rt. The reaction mixture was stirred overnight, quenched by the addition of isopropanol and diluted with EtOAc. The organic portion was washed with 1 N HCl (2×), dried over Na2SO4, filtered and concentrated under reduced pressure to yield the 1-(4-fluoro-3-methoxyphenyl)-2-phenylethanone (15 g, 66% yield). LCMS: RT=3.250 min [M+H] 245.1 (Phenomenex Luna C18 column, 4.6×50 mm eluting with 10-90% MeOH/H2O over 4 minutes containing 0.1% NH4OAc; 4 mL/min, monitoring at 220 nm); 1H NMR (500 MHz, CDCl3) δ ppm 7.62 (dd, J=8, 1 Hz, 1H), 7.60-7.55 (m, 1 H), 7.35-7.29 (m, 2H), 7.26-7.23 (m, 3H), 7.10 (dd, J=10, 8 Hz, 1H), 4.24 (s, 2H), 3.89 (s, 3H).

Workup

  1. customquenched by the addition of isopropanol
  2. additiondiluted with EtOAc
  3. washThe organic portion was washed with 1 N HCl (2×)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5ebb5e05322e46a9a598a67faa0717ad
Source dataset
uspto-grants-2012_11
Patent number
US08304403B2

Reaction notes

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