HCID 66717153, compound → HCID 66716980, compound

HRID 1028633Notes

Reaction equation

HRID 1028633 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[C:12](O)([CH3:14])[CH3:13]>[Pd].Cl.CCO>[F:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[CH:12]([CH3:14])[CH3:13]

Participants

5

Reactant 1

HCID 66717153HCID 66717153, compound

Product 1

HCID 66716980HCID 66716980, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A suspension of 10% palladium on carbon (69.8 mg) in a solution of 2-(2-fluoro-3,4-dimethoxyphenyl)propan-2-ol (698 mg, 3.26 mmol) in 5N HCl (0.7 mL) and EtOH (5.6 mL) was stirred at room temperature under H2 (15 psi) overnight. The mixture was filtered through a plug of Celite and washed with EtOAc (˜75 mL). The filtrate was washed with 50% saturated brine (10 mL), dried (MgSO4) and concentrated in vacuo to afford 2-fluoro-1-isopropyl-3,4-dimethoxybenzene. 1H NMR (500 MHz, CDCl3) δ 6.86 (t, J=8.3 Hz, 1H), 6.63 (dd, J=8.7, 1.5 Hz, 1H), 3.89 (s, 3H), 3.84 (s, 3H), 3.19-3.11 (m, 1H), 1.22 (d, J=6.8 Hz, 6H).

Workup

  1. filtrationThe mixture was filtered through a plug of Celite
  2. washwashed with EtOAc (˜75 mL)
  3. washThe filtrate was washed with 50% saturated brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0e5c7f82a3dd4a90bb6773b022bf4830
Source dataset
uspto-grants-2014_05
Patent number
US08735435B2

Reaction notes

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