HCID 68379851, compound → HCID 68380359, compound

HRID 2178688Notes

Reaction equation

HRID 2178688 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([C:10]([C:12]([F:15])([F:14])[F:13])=[CH2:11])[CH:3]=1>CO.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([CH:10]([CH3:11])[C:12]([F:13])([F:14])[F:15])[CH:3]=1

Participants

4

Reactant 1

HCID 68379851HCID 68379851, compound

Product 1

HCID 68380359HCID 68380359, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-Fluoro-1-methoxy-2-(3,3,3-trifluoroprop-1-en-2-yl)benzene (C42) (82 g, 370 mmol) was split into four batches; each batch was dissolved in methanol (200 mL), treated with 10% palladium on carbon (1 g, 10 mmol) and hydrogenated at 50 psi for 15 minutes. After careful filtration through Celite and rinsing of the filter pad with methanol, the four filtrates were combined and concentrated in vacuo, keeping the bath temperature at <25° C. The residue was dissolved in dichloromethane, filtered through Celite, and concentrated under reduced pressure, providing the product as a light yellow oil. Yield: 71.0 g, 320 mmol, 86%. 1H NMR (400 MHz, CDCl3) δ 1.42 (d, J=7.2 Hz, 3H), 3.83 (s, 3H), 4.06-4.19 (m, 1H), 6.84 (dd, J=9.0. 4.5 Hz, 1H), 6.98 (ddd, J=9.0, 7.8, 3.1 Hz, 1H), 7.06-7.11 (m, 1H).

Workup

  1. filtrationAfter careful filtration through Celite
  2. washrinsing of the filter pad with methanol
  3. concentrationconcentrated in vacuo
  4. customat <25° C
  5. dissolutionThe residue was dissolved in dichloromethane
  6. filtrationfiltered through Celite
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4fe086a3cc0442f9b72131de67a8677d
Source dataset
uspto-grants-2015_06
Patent number
US09067934B2

Reaction notes

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